Fieser and Fieser’s Reagents for Organic Synthesis VOLUME NINE Mary Fieser| ‘Harvard University Rick L. Danhelser Massachusetts Institute of Technology William Roush Massachusetts Institute of Technology AWinzy-InTEscieNce PUBLICATION. JOHN WILEY & SONS ‘New York» Chichester» Brabne “Toronto Singapore BOY care(opti 198 ty Jobe Wi Si ae epoca ein pate a wer hat permed Sn oa he tea ae Cn two raion erm tet trio a rem Se Penis Donen ab ny & Sonne tiara Conroe Cate Potent PREFACE. from fly 1978 trong 1979. he ae very tl forthe aie ad el fom ‘nny ellen, al B- Hopins nd Alan Baton ed teenie nana, ‘Weareespecaly patel van poral y Dr. Mart A Wuonaly, Dr, ‘Walam ober, Dr Janes Vek, retewor Brace Lihite Dr. Ving Lee. De May Lee, Profesor ance Seth, Pofesoe Dale L. Boge, Dr.John Sees, De Stephen Bent Br, Antony Mut, Dr Dna Resor Dai ree, ‘Thomas M Boch, Antony Fe Kater Briley C. Hage, Jay W: Wiig MWhrte,Maro Pago, Manfith Haske, Steven Mall, Thomas, RICK 1, DANHEISER ILLIAM R, ROUSHL nay otCONTENTS Reagents 1 Index of Reagents according to types 525 Author index 539 Subject index $73Reagents for Organic SynthesisA ‘Acetadehnde N-hapimine,CH,CH =NOICH, (Ma wt 99:18, 140, Preparation’ ‘apUnarated aldehydes Meyers and coworker ve Snide hasphonse mine meta fr ythess feta, 121-12; 09)by oneal ‘the reagent nate om and ty chlrphonpaotorm which eat et ‘aston eompounds wo fors a8-emaaiteslehyde eguaton H.R eran Manon Sc 79,2217 99, 3 agen Tomo nt Feng Tn 28978, ‘Acs said, 82,710; 8,3-4:6, 1-27, 18,12 ‘Phenorcoumarins” 3-Phenonycoumaics have been sisined by 4 Prin reason hcyldchySeth them ahtasehstatdpoenonvecces a Ol Qa SOLD seo anki 170-280" equation The ration akin as othe pret 1: Only te tcette of aaldeyae tne ‘Acti anhyite- Fine. "Actin alee Nive, rpare rm Atos ios sion yan it eee aay and pyre with cat by #-Smetyanin. Prine rage ays ae ene "Exner: pocudetnct, Gor HOEOENCANysinemeacHe cm, coved TE cased Act methane 55 ‘Cleasage of ecopoyl Ketone. Cyopropyl Ketones ste cleaved vader seutrl conditions st 20 y the combined reason AcOM nd the mle ‘rametilmnonium fromice or ode (as souce of Brot ') CHOY ae =u a {Acey--oartn-2-ne (Ml 111.10, 8, 108-112/24 mn, Preparation" (oy M0 Ss Eno 1 fa - Dic Alder reacts Two iors hve reprise of 1 Deke Aer reacines and sonst othe rig nar nto ami oh ‘The reagent onl a mvraty ace Senor, somewtat oe vexcne than vilevecatonte The pea Reco, tnantne ne tw stl ‘he snes om tan be deat Oy eathet wh KOM ot amo Iyoieie CH.OH m 20 Or hyobte with ROH er NeOM io tun ‘methanol or eto the ais ebm saholn goad el ‘Tee sranine--one ako undergoes photochemical [2+2] london wth ‘kon, Unrate th esto show no exci Te ts can {eyed wo aninescbutan CHIME 1 ea toon ae eb 0 (r4-Anorymetiyt2aniaopopan, polyme (1) nanoutecte vaya f loexaone A olmeriform hich famine} hasbeen prope sy shown it eguaon (The reatton of 1th ‘eshetanone ede teplyertowndiral shonpiine 2), Asan tb tion? fliwedby mid id desage resin aS} 2-ahyiocetaoooe ‘eames ithe siting reaps the ot yi 5h bse les when pop die ued Thee reas compare favors with thse hanes by Enders and Escheauer y alsntiono cial hyraone of 3 enone (10-1) For «rete reaction sve Bemimethorymehyiety- tie, thiol4 eat Saas semen . eer scent 21D + (Opes = LES) Emly su Paes a ears ey a cope besa Ey es consnocn . ae as oy tones (nee-crn'scostt Ms Hen oe Since 38%: Roche neeeon) eee x. ecthal a shown in equation = Reactions wih thosers (RCOC Hs): manent and lal ster? Atttlhiame ect wth gees (1) 10 frm nut a ih the 3C=S pou ‘lie Thence ca betrapped with meio tofrm monotsetalt (2) wbch are hyrlynd to ketone 3 by eloramine (75) ample: ta Ie, Re ee, > boca ge can Ee canon “The ade ste conve by LDA, with inition of H08, rte stay ints the es sate lena (sch ord ig ar om "Mylan When he abetation tera similar [e, RP =H), itr fp fair ormed The (Zhaomer ct ir aly formes Aline! Anjellonlines sect wih orarolthiun reagents 1 ge rove triton athe than fain. The ection compe ess th Tine evn at 7S Grignard rengans ean be tsed in he see wa, that “ta we Solow nso 1-Additon recto, 1 §-Uostuaedcabons compounds Land user cig Ieeaddtion resions with orenlthim (ant organomapsestem) tompourdsovngtostecchindrnc ofthe tony rep. Thence ‘onverted int aonb ashy cvage wth oti -utxie a H.0 in {Recatot we pon tie vole) andy eniment withthei= LPOrouts, 2 a4 contain he sae crbon sen iplnoneA (Sa sexbl ne ace ‘Thee tramannar reactions contrat wih howe observed on eition of Thich rena Cy Bond rman out “free, alt Gaon " Alumina-catly sd lavage of pride (6, 6-17: 10-12) The noeeie opening of epser by acool cn sho be promote by alia eda etc ‘houns" The reacon then regeres per lemperstuer aad loge fearon {ude ith ascot equation carbecaiedouton0.3 mera te oie with ‘nly 3.01 W-200- amine parched The yd these wh obsned ‘ith ape qunaities of alumine oped wih 4 Weight % of the aleba © (CPeranccrenon seman, oe Anineamoteulrudeophieeponde ceaag of thstypewarutedto content ln 2, an intermedi in stesso 3, whch was via Bere ote he ructere of the nla cannon of he New Brunei caste = os oe Deydroornaion (11-12), The abiy of seal samins ocomet | sonitanrylonnan ta ycevinyl fannie wae rt eparedy Srbach ed ‘oonel!® The comerson tthe iiorouerit! we party tale, te Ee net St Sa sidan of tho Thos ae oxide to dies in 90-95% yeh by ‘xggnation ia the presence of Mere bse slumiaun oie. Bee ibe most story sven ‘Pipl cea? Commerc esr shumina ca fncton a2 tghse ‘auty nega ota Inc cate dlacementrenctos wl Saigimisiimoonin cn ta eRe EO, as nese annmnarnarm {3.8 tech wa Roma a 8 esiareaiee ener bs aaa ihe car separ mice poaeaee Be eel ee tat ee Tia pipenaatamecoannau ovis aptioapente pe EF = Et Ablow clr, 1, 2434; 2,21-23;3.79; 4, 1018:8, 101 doa isis Be ern (6, 11:7, 7-8) Compete dt ofthe one rato of seth opiate with erected ty sominum clride have ben pub Se ‘Seine reper, Sider ea hat found tet Gihorctyaumimam' oper{® ACL probaly case icin eve proto sategeras ellen a Lewis (Opti yee re obtained with a1 ei oh cata ae eaton prio ‘eT ay 5 CHCl are temperature ne pact re formed a he mr produetinsestions ih, andesite senes Monette ‘Sees ge mister of ene ace and [2+ 2] cyclone 12 Dubie ‘Skenestorm(2+2]eydouiductsterespeisalyylohesene hanes Ee ‘The catsyzedene rection ht ben ated for hpreylaton monoterpenes wth 1am tapopeny side shin vo form seulterpenes tthe bbsane poup. An ‘ample the theete comerion of imonen (tte baboons > oe Oy oven Be pemstiin Die Atder cael Akminum cri cyt the rton a 20+ steeone ni butadiene to ie Bj betons instar ike. The fatale dion athe hs arson deesdeton th got oe a p=¢b 1-H 2 ‘Deatlaionof eters cleavage lactones Te combination AICI FAB thot the melo an cleave exer hgh il under mics {eeurion The rection sot sijet ostrich Detention fete ¢ ato, © neon! +AK RSH + boo oR'SR“H ‘Under tee conto some atone re ened 0 o-tythcartony as! Qo 2 nooconencnsen ‘The ow met as pot alae in he ae of the vey seniive fat sabi priclany or deavgeof en enh and bute Soom inde 6 ~ ‘Gh 85) KCIO.8US rand NACI (OD rebmed when hse sal ae sits with Labenen, However, hs moe Lewis tid doe eae he Featon mth nya th scene oe teen prt Sandeene sd16 Ante ce Pd ps eile asa mitre of (E-and(2)-somers Anand I nthe 86:14. The ist was converted ito 1B mnily by addon and aseeqent elimination of exe=cucooen.sen-cmens.cr, $8 om cron seacooen, Newncoocm sw WS rCt Hyd of those ad aesction with yi esa 2 the sex pheromone ofthe Docs tsk mot Akerman and, 4.4889 CH ‘Aluminum clrde-Petuatun pesos, ‘seprematon of phenol. The teation of phenols and oprene wit he eombinnton of Alc, and GHOK (reputed nat trom peal ind K ples) provides» highly selene synthesis of 2:2-dimetylchromtne eqeton 1 NO ‘ter combinations of phenowie aaa Lewin were ound oe compari sth rempest tele an yl” Sgr ye egos Leta 6. Cae, Ce. and Sar Ang Chm eB 1,68 (178; Atom opopoid, 3537; 3, 10; 415-16; 5,16 19. “Alicaleools A Yew years ago Fathima cpr thet 3-panyci-p- ‘sentate (1) i rearanged 12 By slomioum sopropoise I yeaa! te 120-130" The monesomer oft renrange ot mitre of produc icing 2 GH, ‘his reaction has ao been ated to prepare alli alebols (Si igh yl from ‘sores compounds sch a 3 by selective epost flowed by tetany, CIO NN, 2860, Sainte cant Seo Be Enon 3.128697, 5 Tee Sha: Km Se 46197 m7 On 868197. Aluminum tophenorde, ANSC.HL), Mol w.35449.Therengenobained ata ‘hte sid by reaction of NCH} mh CHLSH Phenyl hese This reagent (25 qa) comes single stripe thitser at (6 oa) oe w(t he EEE cuccoscat, Ove = Quon Doma Cems Boron thiophesoide (6409-10) an lobed or this anformatio, bt rears a temperature ot 140" Gefiig ler) However, tstegent etl fot ‘onverson of a-ematurated ete thet, Frames, (oinc=encoocn, PE. s,cuencoscal, ityaluminum phentile!has een wid vty for this recon: exethlaluminm built has been edo pepe rou hers86 Aen he Keen bsighenlbo acetals Reson of thi reagent nit carbone as or eter ress angle tee Dgenhiaceta. ies ae alos! qean~ Tate if thea ret anced at te a or Bopston oe Onn BA Op vucri.cO0EH, ge CHICH=CSCAHA Some of he wel apiations of ketene tact of thi type ae showa a scheme {or sone eatin 2. Foro examples see ihm spatiale, (2 Ey ” Cc el f= ole ai (orn or oe Reation of AUSCH) wih an apamuturated ser ress in 1h rbipenlos ake tach at 3, whic was coveted nt the wopene ese shown negation @ (en,cmcucoven, 2" fenbenescata, ———— Si tant 8 aby) np. 300 197 ST ens Es Cp nd Heine i 398 G97 (Anette 97 oe (9)1-Aniaw--(meterymetypyeoine, aa. ser Asymmerrie avaltlaion of kroner (1, 10-11; 8, 16-17), Ener a _Ekneniuerhavenow obained amon complete met alylaonet ae tons by way af ysttons formed mith 1 Aw crane the peso GHSh4-metyt heptane (av ast sar phesomone fom ets eon ‘Tetyearone? waretanes and syated wt popped tether tape) ae Lg oe =| a ‘Thcrale product wat cleaved bya the N-metyhie. The opel puro shefnal product warcomistenty 99%, The extent ol mymmtt none ‘th he oven is hess ee and DME aod cly 30% THE-ABET, "These metbd wn wed secon for sete aumber of hal aye Prana aa ection The (8)-onsaioner 3 mp. 154158, ant ‘sold prepredin35% overly om tani acd) Reagent hs 1 eoen, ODEN Seppe hi atin en rele tea cotcnyea oa sitet oy A “ atten D] ennee srg er np aa I Decarbrsatie dmertzton pride (2). When maleic anyerce (2 eqn) and 1 (oq) are Rested HOAC a 110, CO, is vie, anon ge poles "4 8 Bouman ab Dour, He 1281 1978, Ammonia perosydllate-SUvr nt, 16-17; 8.18 ain of qulnones This couple covers monoestes of xa {tn par int the aa COR, wich long {acon yi: Nephthogeione inal exten ty cf a 2m 18 ‘ooered ian the 23-dubatited dentine) However, Daly nah ‘thouinonesae comer isto mensnkoyecbonyed products hs etn ha ‘een wed ous othe naphtnceneuinone toa ° OD scmooccoon 3, one ater pega eer allel 7 = (wey ae Tene Sooancon Cae se Mowca Opty ato achydrny aldehydes! ten of el any nae nvlestenion ot nth me! Pyronymetony ‘metncaton! amin! 2. Tae produc ested wi» Ggou eget it he ‘rene of MgCl 1 form the Yeo minal 3A cond Grignard ceaton with 3 {cms imermedat a which ehyrapedo tad an a hydony aly‘opti yes ae high, 0-100. TReconsgraton ane revered yMcange 1 sean Ga, BR, Cage, 0 ee er ae |S OE |e we Son “The igh optical iets depend at eatin parton omen of he mens ‘One svantag of hin oythess shat thecal aay renee “Te method rs bees wed to prepare S)-rontai (2 phoma of certain bees fons). yen 2.-dmetyttepenl” oN ay Antimony ford, 5,9; 6 23-24, ‘Celiprapt carbs compomnds SOF rometes condensin of a-e00es| seth dio earoes sapounds ofr Tbe cogs aay ompounds- BF, tere or TI, mach es fet. The reaction fe bet ‘Serchindrance by abstituenton the vinyl rsp SH lopment amples Rc OGM. CCH) woman 10) a “eno 4 P Dep WF Baan F Det reat Le 1299. eon reagent 627-28, 108-10 126-126; 7, 71:8, 21-22 ‘Meter 1eeleheradns (7,21). n-Aassomiun enon rescues sles he mous. poson nl chromo 1 hs vlume): the rocco rtonton pe Imethny acorns A typical camps i formated in equ i) for vexeon wi Titi 2mebylrenontie “eB [ogl= ‘An inanoleuar eso ths eatin at route to spyloetenones it slo been reported (equation I)" ng, ona, “8D os. eh MLF Senmaic. 1 aro, and. Team 2 O44 12751879) ‘Asiduinthytiene, 1, 12363316: 4, $8256, 719-720; 6,652. Te reagent can be generated convener i rm sorotimetyane adam sie DMF Qe 8 Oem sans:22 Lr Adiaengettae ctiamons ar cane “1 Yori nd Hales, a 389 11- entoncnct, cb--cb er ae onidied to estes, gveraly nih ye eanjen,,oreaiens ae emicrsntoven sen, eaenoea se canfoca $M tt AW Moe, nr ham 8 78199‘Bufacetontaeropaladm(), 7, 21-228 38 “Rearangemen of aie acttes Ths soe Pl sli vryefecive fr ‘qubation of alc neater ot Yoom temperate. The (Epiomer i obaied [Sithe majoribomer samp (om uemEMA,GCH=C, RE (CMEWH.C=CHCH,OAE ‘Bostensoittedloropaadi) 645-17 ‘CHerinaton of eres Craton ot coketera wi this enon get cholesteryl, wi he wu retention of onguation show by 838-01 Steroids dspicementrecions. However in ee cases, the oration i fected wth an Usual steeospeiy, Invenio of congration obtains whee ‘he OH group x entra, bet mataton with enon baie when the OH [roo anal That and Spyder are cone theme pod ie gue. = tr . chy LY a EY Chlrdetrom hindered terol areformedn iow yl probably Pena bulky coordination operon ntermeinte itso) a8 Clorohydrns fom epider. Sect eposes ae comer into coe nis yh renget Dense, 207). The ing opening othe wal ens, aa {ypeconions ae sold hat le seats Seve with yoo ae oie nm ! wo, YP ° Ae Mdm Og 1589110, ‘(.S-cydooadlene nce), 433-35: 5, 3425; 7, 426-429. ‘qetznoelctonization method 426-19) for a spas ofthe pretog- tobe conferin (0. The lay step involved eeronlconation ot the {losin sat cbained or anE/2( 1:4) mire. Trement of wih io copper [vetted tne’, ut wth he natal ciation Uae of CODING - a ~ | eee ey Akven mire of woiactones (21 es). The major product wat szamedto be the ffeized2 This was converted ino cone ia Tow ie by protection othe ‘emethyleney none group egenton, and eqrtetion, ‘e(ltylamine)lnesDiclorabidceapetndienytesom, ALINE, {Cp.Tic, Te sass ae prepred in gunntatine ld he rxcton show ie craton o NSH ARO + NAIR ‘ydreataminaion CpyTiCh, pasty ein cate for hyo- ‘sminntinf lene ith hee lane (qua), Theatre adcacan tote tapped with carton compounds, ope, of con dnd, Dt er are empress Soe w eaten sHannci, EBL. newsen, NE.C. AY and A Neg. J Or, 4.426497 is ibenzyldenactoe) pli), (C.H,CH=CHCOCH=CHCAHY, PC. Mol 375.0, 80 ee: Preparation” ‘@lylaion of ycloheenone” Cysohexnone reas with methyl ‘xecjloptdpnein the pretence of Land metydpbeyiponpine (1) once toatore 2d 3 6D and 19% yes respectively. The rao 2 improved ca 5:1) by ae of exert lobexenone, With S-methygioercnone te 11 dacs obainedin 1% ald ogethrwithonly trace oe dayste prods, g Far, dy (foe es 7 ad bt =e +0. Bainoine,C oes ‘Gullo Nd scat hi ‘Bl aety aluminum) ste (:),AT60 (0) Mol. 26627 “Alllaion Ti cmposn i st! Let as for sctvaton of lero onainingoygea alin wih alystansess Is usuly more ees ae ell elated eae eanje 10 -feny sect, ME jena eer a sosussencnon, ME, a (59,14. Hoainetiyanio)-23dimebonbetae (DDB), consmang-Foune, Mol. 20631, 0, 387/001 mm 9 +147 Sup: Ali. rspasion Enanicetce reacons n cial alent Prous act of ain of rmomenli regent to stbny! compounds in chloe itd {erly lm srecclei the ghst ptlys nee sce with oe ‘tid prin (one ae 18% cand with (#2 deeronybtie (eine 1c)" Seetac ta’ have prepared chiral comodo arta sate sel, mew, and pris snd teed tht ably 10 inde enone ‘ion of wuthn otenzaldeyde OF tee the most ete a DDB fd S5-1-}-3.2,34ctramethonybutne, bth dered tom natal rar ‘Te optical yes depend on th temperate, being Hh te ower the temper tare. The highest opal yi repre i he paper wat 40%, eee the ‘atcton shown eguason @ —cacHorncatas See ‘rig Hefornatsy regents as reat i thst one esantanes 10-20% opty.” Use ofthe chia slr ao permis emote Tcadahion of rpnometaic epee oan’ ator cmpoundsito compounds, nd kstene thinset none cate anenatomerc exes of {295 was observed equation (0) {ing W Langer CN i1-O- Oe dM Semi Hel 6, 300197, Ren Bison ad 8 or, mr Oran Reon NES, Wahig Wt on secs o2 7087, -intyomanirspemombemm(\, 2g? A ok nh, 20213. mp. 10-02 eter loners Tce ed (Go pte tu ih an eps DS ‘Speman nope rtanen ou er oo, PE (aft09 fe tao 20027) Te HP om ‘Nery etc yh a nwt bre ed HE Sicecearorep ‘ron 2) Th oe cere son ca nc yom i" Meh eon ono ‘Sinton span sr ah te nly oy ane tenons eee pcr oascny yn a The to ec neo smo oem, 3. Tae Foi nt et nae ttn cn, ‘mone.2.3-Blapheyiphoeplae-221}-S-eyoheptne (Noro (1). Mol. amctentoaphmih3Adiayhapee Adie oA aA iiggyrcremeerene yee on Both enantomers of 1 ate anible fom the reson of the termediate Popbine oie "Arymmetrichdropenton' The chia phosphine 1 a exe prepared ‘pty azine chelating reget. The ysropenston of 2 wing the Pho flapler prepared fom (-}1 tnd RRCLCOD), (COD™ |-jonctaene) ‘eta pe the highest opi els epee asyamercbyopeston. Ie fonts seer other detain phosphine, bth eatiomes of Tare vate te hercore bath contguation fhe hyaopenation products ante oie. i a “ pan Ge, coon 288 “Provo 14-Bu(¢methorphen-32.4-deladpbonpbetne2 ld (1-H. 21225,mp 128 hyponcope Thereapentpreperedin 60% yell by eno a Om ‘aaton Ts mer (1) of p-methonypenhcnophomhine mae ean Acar ene fr thtin of tices nes of earony ogous ene (ie eters lactone ata and iis Reston oe psy ede18 tpn lncetuing sen of ttune or 2-10 bug sl proceed nile >80%. A, ‘ypalenton tha with bryolictone orm tionsbutrlaons QO, 2-0, "as. tone. Ste. Hon, ad, Lane, al Sc Chin Bl pia oman Cauchy Otome. Sed 25.0 Lawn nd pn, Bal Se Chm. eg 7,223,229, 20,208 (979, 8 ehcp) acm td. Laven, Feat 31391099, “a Sn St 8 nan 50a Lemna Cm A? Aupmctianptententin yo (LL Yoo ktotomamirpe eyo Preparation’ ow) SE. “(oe Opes = Oxidation’ Bsip-mehonypheyetosie (x emidendocecv ore into the coresponding oxo derivatives, and aso of thik into dsuides. Typically (here reactions fod proact f 10-1005 el 1.2-ahd -Hyoqenone are ‘tszedty Tio and pinoees respectively Phen Bydroamine none trososenzee (O09. yd) Pensin amine, enamine, ako, otis ‘Sole, Son, snd 24-dintrpherthyremaner ve wnteactve io o -aopherypbenstpbombostC.isOCANO ‘rte ute’ Te toes fhe tetraamionion st of N- tensile (2) whic ey ener the componente Youe tt ‘DM inthe prio a conping eget prccrsin 75-90% ys hot ecucn,cucoo enn. e1.cH,c00C.K, (et cren.qacomcr.coocats tocs0s> Ho Scat. Soama osc ssw) {aa Ser nd. ene, ha 10879) ‘Baca penteedionas copper, o(C,0.) 2, 81:3, 62-63. Preparation’ Tocotbene Ltda’ nr Ramco oul ined 0 ‘pic ene14-dlones inte preneae of Caac) fn bezone .Oter opp ‘ayo re vst The posed ar benno 6b ssiry then stand 6. Bec and anesomere ae forme wh the er Jredominntingcacpt wen nist. The rogue arredued by secon tonite to ‘eattae-.-one, which can be eeund by NaOH to festa eo ‘entenoes wen 7,9, 10, an 18, ‘Under hear contin nterma opi ofSaoketone io pie on St eh perce t tokth 4 EQ Systinet tat al Chm ee 8292 Muon M.A Mery, JCS Chm, Comm, 1068097 all 5,471; 6417, 7,280. ‘Carman’ Nas cases he jlonision of pol and oro Settytane (1) 10 form 22-dinethycremane (2). The ayes vos Go ccna faa PO Xen ond oneocaliyionandcthenfstion Prenylcloide, OCH.CHE=CICH, canbe wed ‘ce of 1. So aio Aluminum chlorie-Potssom pheno, this ome ‘824. pentneonnte)lkeh-Trmethylaunioum, NCH.0))~(CH) A. Carbomctlarion of layne. nthe presence of the mkt amiss cata metiyimapenum brome ast [riety xine tie te ‘radon produ 2, which omer sly to 3. The ae of stylagesa ‘romie rere inreduction many ci-l-trety acter. Toe pede nds enpeces, reac witha vary of letestui eatscacsicny,+ciisane 1 Gt SICH Can Mee ‘nyse, os shown foe the rection with formalde (equation 1) Siar ‘etn are observed wh CO, abd. In ation, 3 and 3 wedeg coupling eactons, proba ike auyed, mith vin nda bromide to ge denen ‘Src deniitionprceedsithretenonatreochemi thee echo prvie ‘Siu reactions ave cterved with Fo Lalhyessoatuning te flowing termina poups N(CH), OTHP, and OCH(CH\OC:H," At tor, the ci ‘uct formed nly od inomerb tothe rane met eqeton I) The catomctalatin feaction a0 compate withthe presence O 2 double ‘ond ae shown by a sya seran eqation Uh Ci SHE Gay em0 ge, MO NA THPOCHLCH, SUCH), THPOCHLC, Mate am) Cry.ccneHAemcsiEHy, Biiten-betyanmoniam) aeromat, ((CHNACO» Mol. ws, 70091 fanee cil mp. 129-135 Thi soba form of potion detonate [epee ty renee of pean chromate with eabuiammonim ones "Ocdation fy Aalides, The eget oxides enya a ie othe oneondingctby! ompound io igh eld. Secondary ll trom ord too ing sd ut pia all romier are oid now il Yo Mies" Dis bagi ene 6, 56-577, 26-278, 4-44 tog of ecohernedsarequtoral ido is pase By ay tttayen derivative, tied reaction witbin-btfin) onde Apc fenton formated for 4 myo-nia eraei xnsiae (The method oR ou BS MATEO” ae, ee es rel instvar lysine he equator yon pout dil die general wetain the ave ofeaboyerats, Ante! een cramp his ‘sects eshwn in eqution (I) oreectvebensaion ofthe aya rou 1 GIGI same, HE [BBE 0-99. enotarhamnopyraoside (1) "THe2 don erupt Lean neat selves by wie of the phue-tranlor cntaaed testi (8% sie) or by elective ‘enon, belaton, deat el not en). bye Re 8200978) oe ee Biituoractoriodobenscene [loabensene Netiteorencetat), 2H (OCOCF,), Mot wt 43005 rnp 124126" The regen prepared ations ‘edobenzene neat (, SU; 4, 266) with euooact a (53% Yl Hofmann rearrangementn Primary amides ste converted no amines nigh sick y recon wih ths ortant a oom temperature in aque etoile (Gouation The onton trend 4 rece meth wing lead ttc $310); however the itemeciateuocyanae in hb cae aot tapped ae the ‘rbamate but hyalyzed sey othe amie. (Reds rc sGNOCOCFD, +H40 SHES RINK, reo, CL HACHCOOH nyt carbontc nth beemne mans we subject rte nation” 5S. Spend Aoi. Sen 85 (179) AS Kathntia ME aan Rigo ML Ore 4.178197) ‘iseriteorometh)methyleneenpheniphorphorae, (CH. P=C\CF (Mo. wesia3 Preparation: sree OEE A aaa _Biotrifecrometylathere! Tee) pepe nrc wit ade ye to form bineturemctmysercn 30-65% pd lta). Note tha he related phopboraer(RO)P=CICF) eat wh Eetone bat a wih lee 2°. Mian nd WH Shay) O98) 1.3. eimehyhaouy)-Lormethosbat- dene (1), Mal wt, 26049, enon ith cpt. Tt ee econ snout soy neato wth cepa a STH, Com and ome LCS Chm Con, 58197) ‘Barney ete (CH) 1,0 (1). Mo wt. 16238, bp. 98-100 the bas _rpared in igh il yreacon of (CH) Si: wth NSHCO, “Thimehyal eter Tose eben be prepare by easton fn slosbat ‘wih Tinrefing hemor wth pyréniom picuencnaonte 827-425) 5 he eid att pToeenensonc nod is tly cay for sod stale tn {ok The ater formediremved y¢ Aca seve onl xt) The extn regis several dys for conpeon. Yi of times thes ae "Pee B.S Ba and LT Lr 26 9H BUdeinety ty) Himalaate,LCH{COOSKCH) (1 Mo wt 254.35-The smi s prepared y reason eee mont’ wth bait ‘ther ato Kev acide? The reagent corners id shies into prec tat undergo hyde and decarbossaion I he presen of wate orm Beto ‘eB The yl smal re improved bya a 100% enc cores" acocricoosiesnts BO ncocu.coon ‘lteter (1). Ml wt, 346.98, mp 102-104 Preprtn56 shit meget Debomination of L2-diiromoalaes. Bstsimetystmercay de Iwominaer I aiomaltass to seine” This recton hat beer aped 1 ‘atom an! 12-diodoadamantne @) st auto sdamantene (a) Whe eformed in the greene of 1 penynobeanarn, te hydrocarbon 3 ‘Shuaned in 30-35% yl In pmol, thi rout cou be extended Yo olon of ‘nce ober at Bred alkene & |p) $ GP En. 9S Anand Kut nC ge ncnnscEtere RA Jick, and RW, Waa Orme Ch bea ‘ivetdyety) nonoperoxsllae (1) Mow. 258.4, Beeyer-Viligerondatin? This eager x gener sero o Cares ait (wonoperonsr ace for BaeyrVlige natin. Linton ar that Jo ‘Mobopahareatacke, that penones eat sgeshiy, a at arta ketones He bytes to pena 1.3-Rlafietilglon)1.3 bane, 7, 27-2 “Anthayclinnen” A hey oo nase of scouSon i) or : wae Seon — ( Reaction of his type habe ben reported orn -romokeones withirn extborlcompouns ore copper soune acta (157-138 Br ‘Bromoptopane sopropl bromide), BrCH(CH,) Mo. wt 123,85 ‘Protection of ents of Bete aldehydes” The tecion ot D-ydrony: meisencyeloexanone wie 2bramopropane and K:CO, in DME ges 2a Protection of phenol An sappy ches ae ao one by ree of ical with 2 bromopropane tn DMF The protective group scene BCL ie (ruc, at barf abe to SC, oe TCL under tev cones. Hie recommended for protection of pheno oupe ding tmyiton with Sieromety! met eer in the resem of SoC SEM Geom See 168 Pin,Aeuopopoaisyde sylane sca ect). ML we somatic mone) ‘Getpns nsn Tear drat ot rp ety sit Rete npresumorde 8 #19, ane cnet an ero telesense tcperth at pry habe Ste 99. Tae ‘Sater second ne roscoe with sone THE Sane b-s2 OP =o +R Mund Mei seo ewe 97 070) -Bromonacnie 17-802 40-4;3,34-36:4,9-$3:8,65-66:6,78-76:, S740, 8, 38-36, “Acid Bromide. Aldhytes can be once 10 aid bromides by NBS under lnadton For exempt reaton with bral retin bee Bm meahcH0 - fecatcone MeMCONMEHLCA. ‘Bromakydrins? NBS in aqui DMSO is wc for preparation of bromo dein 818 4-35) CySopentafepene» Mahl mages eriormertal ant iied species e bomonqden By hi med Sod meh ide went of ? ord he cid eve ae hihy mater ep 3, nich ani hte mene pesdain,Prscoens (1) cts line of ertin aes 10 molt p> cecil to premature ada The hy race cpoide 3. probate ave Italie of ha ow bees syathesaed NBS eatin ofa ggheoes THE ons bromatyarn 2. which wh tested with Nall alors 3 f 8 yield “Asenpistapeeare By MCPRA, VOinae,rbeyiyéroprosie oF Mo\COe ‘Pauydroperonie oxdtions were wus * we = A of BE Sets eidaton Onto he I with POC apdotber CVI rage ‘mucous NBS (Seguin) xis the secodary lobo! group wel 104 ‘Srton pup nett) quantatve eld Ararenitf hideous, Theil team seme ava precror oth 290d 9soancpapearane (6nd), ‘yl serene aoyandes poduced om pecs pose Hen STL Gacrind as int ore 4 1972 Neate Dimas ee an nae > J wee [N-tomosucinimide-Dimety formamide mination of arene Nn Dh weal for mosbrominaion of reastve sence and a0 of phenols and anines Te fcton rt wel fr mone Smits eo-tdpintonpemirfr danas Second oor “ obo RL Mil, YA ta and. Wag, 847919, cette 18 {dol daydopyane oa bome-aerlcten equation “O= “hic now reacon wat fit observed as one stp in the conversion ofthe emacetate Hof saan an irda pce no he clone 3, posse cil ‘meme 0 posh! Ayes msm, AAO see san 2 ae "4 ony ton 5. Seam) el SC, De Bromotimetyine, SiH) Mo. 155.10, bp. 7" Soper: Alte, iy! bromides? Alcohols ae converted into bromide by ration wih eomotetan (14 un) ls CHCl at 25-50" equate I. The eaton ‘secs with iverson, Terlaty adbearlaloo reac than pry Sraccony as, Bromiley are at formed ender the tame cons rom Inet tesa akohls However times orbofomat camer ito Inti forme, HOIOCH,-»HCOOCH, Unike fodarinetyintne, he oy ROML HSIEH aR HOSE Ase SOREClevage of lactones ond carbonate? Lacon and sooner reset wth ‘bromotimethfsine to ftordatromocsrbonie so derivave caution Dad ‘romohiia nether equation I respesinly eyhs ihe donor renct with bemoan. data eats in alot fasion wt topes, but reactor wih tyre carbonate the main pee 12 -doethne equation Il Tew Sromocsrbonvnte dervtvnareconerted Isto aed herds by reaction with SOCI, equation th 0 Cte Sear metaesomc ots srcmicoo o f 4 Lene co, Se bic, Sctectve phorphonate eter dealaton” Alkyl phorphonat eter ae els thy and early quantteely cleaved by bromotinetinane nthe pesence Of Miylearowate exter, caamates setlener, ketones, nals, Akai Soot eachage unde the section sonitons The roving birth Phomhonstn ate hyde in aceone hy ama ex wae, TA cm.00ccy,r0.08, a4 aHCOCH POE NY, ay * CHMHCCCH, HOH, "0 ro Wee eg Re A Dag a Whe, 1-tsedey inet tainiom tabaorsborse, CH= CHCH=CHSLCH,)BE, (1) Mol 20202, ens Sone Ne am Fpuryanclaton” The nat of lesan reacts with threat) fovm thea -nanused epee 2 wth dalicemc of ney sie and 2 iste of oar containing product (9). The reaction ge an ep {eral for esate unhindered ce betones bts ntobverod healt ‘fayeicketones Homcver ts pomblewshensstere senses Anevanple "he conver of pheylcealyde ta dan 8,insomerat ow ye ote cb oe ° can cH0, Joa ote Yonec, Fpowanhtion hat heen ese petowly by ivamolecr Dares serie at snonn equation lI). LD Beh 4‘-atonsbisdimethytaminoimethane, 871-73: 7. 41 (Cerfevlaion.Bredersk’srnpet has Bech wed i 3 simp sath of ‘y-snhonyltaris acl (9, anneal train ed pret in patho from -patamic acd and aval commercial tsconertedDs taco ih hs tearsfoems 2 ito the wichlorethy ester 3 in moderate aed. The srhess of is completed by fection with bene haba and wehflamin flloned by . 4 AOE, a WAL yg NEN ca cong eccnea, ‘9 -Buty9-orableyeo3.)nonne UD) Mol =. 178.13, Sapir Arch “Dien Regioseleivehendo- coupling of alkyhlithiamsand| ive haides cam be etd by pear corserson othe ayia tthe tion sig nate sia eacton with 1" Reaction a he ty oaihium sompounds wpe sty fords hen--head coupling prods! wheres he sinalyeopres twos yield aso coupling produc” ‘cot nan a Sa) | Batglcborodimetne 4, 57-5! 7617, 5, 26-95: 6, 18-2 ‘Selective poco of primary lobo Two reset sts of rbrgaal (ay seqeedstivemnoptetion ts pomary dna sme wc wax oe read bye of his bit sane Thus eo 2s contre nto he money ther quale yw by reaction With ruins and Indo DME Smtr, he a can be seectely potted oie 8 eS Protect of vi al Sever bt hve recent reported mignon ot ‘-buyemetisy protective gost bonedeoien Tha In 2 and 3-0 utyimetiyy eas of onus can eran inthe pen of the pine’ by a tame veacton Ohya mt be need in the we ocean eens for part protean of paved “Rogie ho ma od Se Gn TTS nd Lene, Tea eter, 598 (70 SES itee se Rae HES en 08 ‘ut clerometil eter, CICH,OCICH,) The ster can be peepard a & Anton Urs hy tess of NCS with ha met ster hc 39) The the ‘komponc on amped lionProtection of hyde! grape. -Buosythy ethers of loss can be btn y rection mith bichon ete ad eal a THF at ‘cial fe sable to Rot ae nd, theelneseecve deprotection of ket ei-enatve soup pole? H.W. Pn and HLL On 48,3966(978) bimetity prorat) Mol wt 214.73 9p. 38/0.08 Proecon of dar rupee grouphas ben eed ingly slo rtetion fh) rows 457-888, 176-177 6,75) becase ste greater tity to solos tan own ty he ime rap. Tey Save een reared sigue clr, ath toric can {A} shoul be more recive nd deveined 3 mead fo he reper shorn equation (The perce has noone character and alent ser of ‘he metho was extended toa sya s-buy methyl perchlorate 2, bop. 45'/0.1mm.andtoent-elllperorte wich prove oo umteatne to ‘Both nd (2) convert ab, evn ttt one atthe cortspondng ‘thesia the presence pyre without lormatonakeen heaton sere "api than tat with -buyethy eho, The ethers deed foe 2 ace Unusual sable; they are 2% lated by al in DMSO even levael tere "ures But hye be cleaved by BF ethers CHCl at 0 pie horse ether, bleh tm he hay by NBHCO, at T-Bone R Tah Og 8 3 878, ‘uty yaroperonde (TBHP), 185-9; 249-50; 3, 37-85 5,95-7, 6, 81-8; “sien In compro with rented oarces ono so aha H.Os and H,COOOH, TBHP s sual ae to handle: one ofthe rot ae Know the 70% TBHP aval sommes Lac, Aldo) bes acute reac (Gihorctane) by saotopc dying. The procedure is dsb in deta This “pesldaton, The st steps synths ef petsleactone (3) eu 90%. va, 8H RO eH ee ew Aly! ryt ketnea” The sdduts (2) of aromatic alps snd cyan tetas canbe deprtorated wth LDA (THE or ther, ~ 78. The esting trios can be syne ty ay oaies, brome, and toss in god yd Tae rod ar aly at ola at are hyoed by site eeacos a ‘enalimetslammonim oreo ketones in ite mainly of 90-905 cyan” The anion ofthe at of cantrinety lane with benz de reacts with alshyer and ketones to frm aclon al eter (2. by way of = {0 all rearvangemensa->b. On hyo ayn (3) are otsined a ah Thiyanaes®Thiccyasis are obnined in ie ely oer BON by te scson of ley! chloe with this alae in ry setae (0 hot, 25. The SSvetage of thi method stat othionyanates ae nt lore ad that e¥e0 Sematie ocanatos are cas preare. The paper reports that the ost St {teary method for preparation of silent chides is teat of ul ore haba or cide (0-505 ld {Dever W Hentai. 04. Webner, Bt 18, 2085097) Siegen Reem ying tec A elder 6, 15115258, 15-135, ‘Phono lorraine (1) The pots res min inoniton to the eventing alote,tnadatine the pen of ode (CD), Sowever, rel mun in dechorinion fo romaine (2, whch abo come ‘sina milo (30m photos The rata conversion 110 2 depen he ‘eon and the ate flowy the ore Scania yee ‘Teyeodertin. Since thee codeine erin hee ol he ey aa (hat be comvenion of 1 2 ues lace wil he acon compe.” COR, OND =O00 Acslaon of Qrecodern, The sation of Bjlodeaen i modesty scceerted by Round mnivonbenyt sete, mNO:CH,OCOCE,. Reve) yation of Beydenin state comparable at ‘eoerepre The eyeing eget inthe pniropeneser (Df erolaamic teal Thtrenget wa chen bonne ersaene tong ono with te ty fecyedenan. The ayn iv acsrted by ,000404 sompred 0 yao Lin DMSO 1.0 alone bufered tp 68 Ths cyndetin can Os, MF Comic ane R.Br S68 TL 8)D ‘ior psc rlvens hs bee cramined! On ding that o one ying gent |sSastctory forall stents HMPT very enon to deseion; Dt dition ‘Homelcam dic olowedby storagconer Amoleclaraever per eateab Ay solbent Molla sieves te abo recommender mination o water rom iy Stent urther dessin cen be accomplined with olor Seve. he ease of sete, bors snide was found to be the denen of ‘hole, Ody enough this cml nt stair forthe other sent rs 1 8, 3965 (1978, (1,8-14-Dacetorybutadiene 1153-185, Naphthalene re The Die Ale cation I tactonybutaciene (I) ih beneyne gered Irom obeneneasonia carole, 1 6) ges the Slacett of 1-ayaronaptilee-cir tl 2 i 53% ld The product converted ito 3 by reaction with hydrogen perotide and aac amount of ‘smi eto. The montis of 3a combatant dy eeatment witha ‘Thisepowy dt hasthesteteochemty oundin heen pony tore ‘metas of wat hyoarbom. The Gisyate of i covered nt te OT DE OD on a re : SERBS ‘6 10 Diahyibocestitoromethancrtlonts,R, BOTY These ise ae pspaed by react of aboranes with ii any, ‘Strerlevivealdl condensatone Mahia al have reported that ion ooherarameat neereeemeatiee sie een gery Scien ene came eee Seana een ee ica Riese ramen Cimon | SD rtmcny | : W Fewer, . ce oo lense ata -pecnca « Sina sereoetve sos ve een obtained tbe ‘vnylonbornes drives tom Shu propanthiot eatin 9 Cer oo cnenbeens Bes, | nto) a8, ndesaton ana)" Jucalscicn, +ontccu pan te Chm Ur 97 ta, Fi SM ima nd Manne, oan ar Gah Dewanipaiadiom cre (C.H.PICD, Mol wt 36885, mp. 120% Suppie: "Aly salfonn The reson of.) wh arene cio osm sreneslintes in THF onthe presence of thi pallet and ‘heyiphoshine els in ajc sllones. The moe ntiated nome oe on cued cimcurcatsoat ay ond cneens 1.5 Diaaieyo5..Ofondecne-5DBUD,2, 101 4 16185177178 6,158: (Celoherediens The at dept in tse note! sates ot damascene | (3) om dnedon’ by way of required entation a anal yr eo4p td |Achimination of cet ae. Acrate MnO, proved be supra yin hlorchromate (40% yield) apd to NCS-S(CH). (447-89) which cane sh ‘nation ofthe Hyon yop The at sep war elect by DBU are fo 20 oy rican Catbsy asi on be tered by reaction wid sy aes tod DBU i onsne 25 o (sunt I) The reac wie api 19 dered or nab sch spo BOC- of CBZ-pteied ain aids ile lnvarbly igh retytarine ol ie baePesama te hyo ‘ded comps sf DBU sod thes lp sins ram the reach. The [Dn cn ne rene by testa of fe hydrobaie wih sou hyo Perens eng terra Ct altel hela cee aoe races eres = pee blading dae (bret eee emeeenea Snes whose gle ae crea eaten teOM = Qh gs aha nt Neo, Zen 059795 Desay peronide-Nihe bromide. “Detain oles Secondary abo at one Wtonsin 85-98% ube compler bir meienyethne Ni {CHLOCH), (Alaa et Under the tne conan itary less re ode to eer. However 15-25 eq of Ne, bse, shes cn be obtained in remonable Dibenlammoniom teoreaceae. Mol. 31130 mp. 1398. This sai hulncsin Tie sek byrencton ct tuoousts dad eayamine the “Mn condensin. To fag eigey ete ctlng the lt cyscaton atte dee Ehmiationof he etranyropyanoy soup mi 5B, JO 4 298811979) oe ttt SN ome ‘Dora, 1, 199-207; 3, 106-108;9, 76-774 124-126 8, 184-186; 6, 1-162; of acyl stereochemistry. The five contguows stereocentes of ide- ‘yde an ncatins ia Ki tl rym of monemin (6) wer established sterols (8 dsteresmet tif K 1243) KS argues atthe ono! -cen.ean, enso0e< Now, \ oid YOY noc Yen, remtiale stereos ots rndortonsae the peferene for these yim to dope conformations sch Af i which hyrobraten os peeentaly trom he em hindered se, An aslo eal as eh pte Feesus by Matsmot a 1 eryoctets aon Reduction of a-msataratedeprides Ntsc sles can be epee by telecon of spranmarted cps Aiba ee at oly moderate. {8° the method terenlest i th te (2) menor. The reaction aleve oan connate edition1.1-Ditromoatyiam reagent, REBEL). Homelogtion of ldcydes or etnes These eaena rest witha. ketones 1 orm brmologaed Ketones ‘Peample 2-Diiromomethy esa cori, qn A), Mot wt 31240, mo. 59.5-545%, The peoparto’ invakes tromiation of etluie acid” and then et provevon' Pinay and secondary yon poup ae etre by 1 inthe pent of pia (71-92% yt). The osu selec fr aeyation Frimary wero secondary Byars functions The teins 2-3 romonetifbeasses2 te doprteled under nesta condone by aver per ‘orate mediated nsoly 4 2-tormylbenmate exes 3 (2.6-uidie oF 26 Cotcine fed to ainaia » vial neutelreacom medium). Asan of ‘morlne hen ea trap dean fhe oli igh ib (57-90% yl wo examples This step probably proceeds by way the morpho Tne auc as fooled in equation {EL Ee 222 nro st e=:0) Deprtonaton Tiscompou both ipa alee en coe ‘ube deprtonaiedtoaviny oan alan cra miro oth Homes ‘nea ihn PT he ont Pt Team serves the eulet of OMCCH CH Lemans] 28 caoecnonosn 24.D: stay tegen, Co (0, Mot we 22031, meOxidation of amines amide ei sey dil oie see the semetinene ssh ofan amine fo obtin the soespondiag amide. However, Simehylanine 2) condense with 1 to afd 3 in stacey Ve. Ras tuyeed onaenation of 3 ett ia amie) with operation of 1. Tw ‘endhiowstoroeypension can tested Potassu-brous Dal yes 4a SE°HS¥ eh ut Hie covered i nly 10% yl (L urstable under these ‘cmb Alteran, thecombination of KOM ethanol leads 4i9 15-73% Jel wth boner reemnery of 100%)" Dinuntbort 8)BOS0,CF, (7.9192 ‘Sremtetie ald! condemations. Rete: Teast wi Lia the presence of ttylizoreplamine afore (2h eater wth igh terconelecty. The ‘trates act ith lyn to ford primary eset ste ondaton Sn alkaline yeas sme, i, BREE me In the cae of cyloberanone the ysopenteryl boron enolate must be ‘mployed 19 achieve igh aseeastlciy. Soe aio Dilton Sa. B% 26-Dis-baty-tmethypyiine (1). Mal. wt 20535, mp. 31-32% 153798 men Supplier ek epi ge ae Qo (CUE NZ CIC ‘shin soph he sen i ne in stein ia, Piven peas aco so. caren tae eens “Te combination of all tiforomethscniosts ad 1 romana or methyl fearless orang wo eae pope 2 irate 4 nom haat te Pha rite ene suse ohetane n a a pie tt yh ene a a mca nae Sena al en ' Pksgoencny “EAS hl hg ek St1 Dann grant Dlcaboayt lopentaientcoba, 6, 172-173; 6, ISIS, 7. 9495; 8 Phenantrene derivates As pct a ogra to determine the relatos ‘erneen sina carcinogen of ply hyroaons, Prin a Va ara bave pepe und rom iStheraiyee, Tmetion of the ioe wth {CpCoAC0). high tion) pes Lin % yl Ths product converted to he tune sibere 2. whch converted ino 3 and dbyonsaive photoset The honest 3 snd are neat f rind ing son, prc 3 “Thehyorourbonabo der nchemia bchavir:Sydrogened wie nly 64 Theater hytocrbon hs mo mage Propet, but isa weak cacogen a C Seco = CD _Esrone synthesis Funk tnd Volar’ work on costigomeriation of ist menystyDceslene anda I -hevadpne,17) har canned inte sybees ‘tatetone one of which sow the sie regan. The stesso 3 ‘oedesatn of #803 Rad Bee repre eae, andthe problem remained of icing enble madicatin for earone syshen. Use of metboxyvinet ys ‘nebo rer thn I wsesplored, bet ree i he used regis {Ghd loo 2-metbonjestatenone the major Sal product Brominaton of 38 ‘pono, but he major podact esata rm depen fhe rather than {he Stimetiyt pup. The sncened seat ofthe poston wat then ‘apotdty leche reason of ah luoroactc sid at —SPTC to gve and $ lata 1-9 rato. Ondave denaze of § wth lead tealsiiorosceae) 282-288 prcees in alnent quanta yc ogve enone (6), Thi quence the shore yates date ot dvestone ve tp om ?-methsleyslopentenone in 20% eral yl and scents rom 1 henane i 7% oral Pl. hatamieepenentnantninthsllne inert 8 op et “ehh oe | ot ie 98580097 Dlarbonyeydnpendientronmetyiimethstaliniom krfaorsborte ate 35998 yeh wd soa se oper ser Pepaain: BO, cqracoyensests Cyeleapanation Cycopropanescan be prepay reaction ci with? ‘eu ft regen dotane ot refae Teeaton sterner” lepatcont cpteconcnsen,La ctentneenit Din -arbombesacrbonyltcbat CoO), 1,224 225:3, 89:4 89:8, 201 basse, 17,9, 99-1008 48-180 “Acyaln of then and athe: Dios a alkynes can be sted under phase antes cotton ycvhon monoid met tedden he pee of [Saye mountof CoO} The reaction with ayoes esas ina nyo 2- ‘patente: he protabe mechani shown in equation ( EE oleae | 1.3-Diene ae sya unde the se condone a theest ssid carton stoma ge exe an (eons ence WO Nenwenenmens W Neme Cateye racine with bydrllane and carbon monosde The reaction of lean, sp cher ind sschydes ah 2 Byeoane a arom moni Chateed hy CoNCOl ee Ruan Rh comers hve Ber rovkwed 8 references) A number of the mote wl wanfomtos te semi in epntone AV) cy sews “ Ce foanasonso 80 "We Ce a 16 Ohm C1 (978.4 et). °S Mulan Sowc ape: hom £1,800, em: Diooal thie 5185-89. Corker euealet Genero gem-coraithiam (rom 3, setlrprpen tnd ium 22 evametnppenie. nthe ee ses tn emcaoinocin 8 - trope (3) wth ads. Pee eee concen1 Didtetdptdninien Diclorobisteyapentaden bani, (CH, TIC, Ma wt, 29.00, Supe: aa Sem “Lacione synths! Tie TAN) complex can serve cats for hon Imagnesation of uve o honoatie abel, prepare by adn of ei "iy-Grgandrengerstoetones, tyimagsetn bemused the ours of Imrenesum hye. "The surbonyaton of he oganomagnerom intermedne Felsina oF lactone tequatin Jenene te $y] = 32 Dickorbiscy opentdin!itenia-Lithiam bro de. Hydrooraton" When thes eo feagents ate med ia THF, byeopen cv and satin of ole! tn borom comple forms The compe ‘Stayees te hyohoaton of aloes with LIBH, wo form Uae aye Iie, wich are converted 1 alcool: by NOCH, and H,O. Te relative ‘eactiaty of alkenes i feminal > yee > itemel Te resco ives aa "gen Sm M, Hato Yt Chom. ete 149 (1979. Dicdrobieyopentadon tain Triana, Cp;TIC AIR, Zt-Diallyatones Monshyiahenes of structure 2 eat wih 2 eof seaget Lin CH, st oom eprom alkenes of ype 3 Tae ean bjt weve elt the il of 3 decrees athe ie of Ris nts. U8 “ont wih sme fncional groupe: Frome, Baroy and eter ni 4.1 Rte Wi md GAL Whe, 1, 38979 Dict aghenphonpiaeeroceae paladin [Pedy ‘Ths plaiumdD compe prepared by react of bsactonile bora lav with 1.1 -blphemipbosphineerocenein benzene: ‘Cos-coupling of Grignard reagents and onan halide. Tipline fie of scaly! Gngnard reagent Use of lctakstpberyphonhae ‘lau o elorobainkenypbspine)pladin sot etl Pee Diclrobaiphentponpnenchl,(.HPIENICI Mol wt 68428, Supper: Af Preparation Coupling of Grignard agent wt antacid ler compara Ti nh hoophine camper ete coupung of Grignard rageats mh eal oa ‘xuerinings cent xan: Pcuccatscr, + paca cegtet, cso.c., encacy ‘Teecronr coup hetncen alc ses eal Ggand regents rosea re ready In he ae of hindered al suds, NICLIPIC, i ore este thee NiCHICGH,PCH.CH, PICA) bathe ater eae more te for ng with inal met tie(eiphesiposphinepatinun()-Tin I) elride ya, (Cl Sac 28,0. ation of ey lehaeTi complex ctr the mthorttion to rearanged all eth eters” 2) an ‘bum DO) 1.218 ais.a. 12.073 Oxia eyezain of arldencbryrlaione ignans Reason 1 with? spr ein Smee aon he eke ce ne ae paogrtthe scp naan as nea aun ; wy Phe wbacs seen, Ad L TOG Aryl fardes Te generis 2 when test a beset with DDO rearanges to T-orobenatelpytene 3]? The aiurie speared yer rangement of dol wth yams uae DST. Sir eee wh?‘.8-noes Too soup have reported the sian ofl ena ether | ‘a-unatrtedActoes wing DDO. Ths method i most sable for eyo ‘enanooe deve, Fleming and Patron” repo: that ve ze general Imposed ty aon of colin (15 equiv) which pesumaby removes the ‘yepatnst DOOM, Ths lt communication ns repre provement the ‘parson of sla the hinctc or thermodyaunic ny enol ees by Howe's 21Diste sees Atnmadne 18 Odin of ge lesbos” Anew metodo hs ceton vane woe ‘ulyteamoentof DDO ag scicbemene-uatr sem vith psocid {or repeneraton of DDO tna DDO. percoquinone monoktele McKoy aod Talo Dave prepared thee substances fey by enaton of akon. or aslouypheal wih TEN 360), iki his oxidation can be improved dion HCO, DOr Fe, incH,OH can ao te wed nin seme cen ssc where FTN fs ep: Dehydrogenation of 8-pnazlines The orang His teasorme ino ‘helsonatoie ty eat wth ah of DDO inedung ene o once a {8.50% yk” The is re higher than the sep wing NBS, bt copa {he to those with Ma, However, DDO inane vale than MeO, To ame To XA cao oon MS Neuman ¥ 5 Ro Kanan A 1 68 99 Lema a0 A Tne Mk A ene nA. 909,ichlorodiettytaminboran, (C\H.).NBCL, Mol 15385 "Diectd ale condensation Ths borane converts ketones ito iyo) aminechoeshormes ome of which ae able ss compounih such 1 {lrmed tom sjlobexanone’ Tew produc react wis aches at oO femperatue to orm a atte of ade (2) which he etre oneal "The reaction a ecard out as a one-pot procedure. The ketone, ancy, ‘the horns nd og fitness tired fo 20 Rous a CHC 27 Sagas Toyoan-andK Souter Som Com 583 (1979, Dichlroten, 1221-22; 2,115:3, 87-884, 138-138: 156. ‘Cyclon iene ethers Avex, horketene, enero | Svniyloy-2.2-siehrocsctoatapones, usally In gba yield. Cysoadtion does tot obain with dhoroketone generate fro bless hide aed tr Sing opening ntemedateesabuanones” Cictaditionw alkynes! Dihiowotetene, pence trom chon ‘orien 156, art alkyenopvccoutenoes Threat css ‘eters wih te ile bond eyes "exons eene Clason reerrangement’ Dicooketeae (1) est wth the lis tule 21 ge te expected (2-2) econ (9) ae the Spr eter ofthe ‘saturn ac (8, Theater produc xen trmesby» Case eae ‘mente 1.3-cpoer increta Podesta ao aan om iets sles int, the cine alter nye seed ‘ters are wl le ‘This now rearrangement hasbeen sued to thee the 10-membered rag mci phrase 1) he ome {he(2+ 2] plain 8% ye thems podut th lasone& inhi he ube bod has the (Erarometry. Ct Myoention of les he ‘ele dechlormted actone Redaction of 6 with inca nd ges. The finale i the sates of 9 ined (Z-scan, ete Hy Iran athe presence of atta open das”ates onc Co eu, oF = 4m Kop A Haus, 048,317 (97 2A a Di ef iehoromethy ihm, 1, 223-224; 2 119; 3, 9% 4 198-138; 198-200; 6 roa TAtkynes Pinay alls tales cast with chloromethyl the proscrcof HMIPT(] cabin) oform holga borane 0-2. Sele Severl methods hve been wed for dehochornton ofthe prog. A ow method the team with 3 equ of rebut to form Iie Dicom meg ether, 2, 120; 5, 200-203; 7, 98-99 ormplasin of nstrsrd lanes Unsaturated aches can be re= rt equ of TC, eget I" Theenasnae te (consgraion repre of cer ‘icra (1), asengterpene ache ‘The reason not apple al/riethyianes, bar itcan be ws woken Diet etiyitenemalonate, CH,CH=C(COOC.H) (Mat wt. 18621, TS-IE/7 mm Preparation. Soper Akh, Fi, Arpt 2atcdesates” The regent cin te wed for sterscnestc sytbes o 274Fe and omer hye hae ncn ey Seb, free Pore pananane pS et nnn 19 foes, Syn Ca Na 28 8905 ‘yt ins tnpeeannontnpetonnt, 11.0 fect {Th pws Cabana inate oan Wi Heetem-Subuiaton of C0. The reagent eat with abou compounds to form? anatiencs (2), which can Be late But ual omer et ‘mesalenomins (3), which react ready with loti, shown nthe exam ee on Heat or nc CY os Choncmon cation Diethyl metbosyethxymetyphenponate, (C1-0),AOKCH,OCH.CHLOCH,, (W). Mok Wt 22621,bp 90-3702 mm, The phosphonste obtained 7 pelt bythe retin of methonjetborymety chord 227-229 wih ethyl phos pte bur at “lomaligeed oldchydex! Unite. dehy! mboxymetiinhomhone (G.HLOnPOICH.OCH,, wick des not endergn Wit Horner eases the igh yl. These roduc canbe comer no en eters of shes (3) ber bp heron ty westnen wih pos unde Kluge a sh ropared he led phorponste hy eva ropyeayatin of sien bust hyonmehyjtephnae- Ti reget ha the advantage ove ta {Gat he oa ees eaesponding 3 ae very xsl Hyatt a NC Greets Chom ee, 524183), ‘Det phomphoroyante, 2176 192-193:7, 107 ‘Celtion. Active metylene compounds can be C-epted secty by xtc nade with det phorphoremandate (2) 9 camtnton ith ‘tyline. DME isthe pene volent; TMEDA of DBU ean replace ‘tylmine” Examples <> Fi WceRenscoonsiLecoocsos > ERiERen.cocmeooc, pees : SESE andenen,tomencnsen, cMcwencoon sic’ ae eaMcHLOCOMH xSeeker a-amin nile rymhetThiseythsncin be conch reson oo INN-Dietyt-gropymlamine (N.N-tethylaminopronyne, 2, 133-13: 3,98; 5 217-219,7, 107108. (Cyelaadion o an mranctuated lactam. Fl ta have extended ‘ondeonreacton of Setylamimonkyre 19; 7, 107-108) tose te {2 pannturtedtacam 1NN-Dietyaminabutye cdr with tam 1a the ‘tence of Mbt aerdenanine 2. Thr pout shydoled andeterfed 0 in i nani A, ei {Cetondaions of amines 1 weatbeves. 1-Nivoesopentene condenses wih yamine Linh expeced manne (8,23: 107-10) to and eyeautene2 onde with § to rd ions 6 so 7 in 25-30% yl. Nhvos ae ho ‘sine rom the comemato of 9 and 4 with. Thee ines a poocle Sexe 125 chow Co, 3958 Dietyl Leimetiybislosgethtposphoate cx.6H-PovOr; th, The sexgntispreprey eatin valde etl inet phere Rvs suteta Phonponss ofthe pe seve ws acyl anion eile “Thatihinionllowedty aston per 2, which cane iarae ketones 3 byte, However, the allylation mast be contacted at = 78-20 to peveat 8 ron Wit resrangemet to 7 defia ‘ :been ust prepare Ketones fom aldehydes equation W eaneHO+S soe CHLEHROC HL, Be SE eon Dituorometslneipheyihospborae, 2.483 ‘fe Difuoreatenes The phosphorane can be gesetted fom CBE, and aH Ieeonvertslehider an setae ketones into go ifeorealkenes 1.1-difuoroalkenes are ~0%. The praca cam be reduced selectively by sodium ‘sn methowethoy luis hyde SMEAH) to I-manoioratenes in 80 95% ied euation i? wemsasn ), saw 242.17. The rnpet prepared a by reaction of 2.2 2a {ohsoenllonte Alisa wh LDA @ equ) a —78° CHP) ‘eke ec The reagent hu been ued for bahotlopton of cuts compounds teow to keto a estion I" snc Fan Le, te Dinydiatdrsieipheypbonpineratenlim, RUC) Mo wt 115225, Prepaste “Sly ena hrs? Sl eters of peimay aly soko are homed by ‘ised compro rateetam at 10715 (1-20 boa amie of 2) and (Evisomers a yl na ether n meh he forse me ely predmiae, Sevnosicto, 12:Dydtaimetnh inept (ol wt 162 Preparation Ae, sverifcation and lactncaion? The ide 2, Sine by oto of ‘ett rp wit carbine phenyl forma thier) nd the Spl soase Reaction of 3 witha to form 4 posed ia Minos quinae witout ceo versa 240) Ths} en ate ‘omits more ete than he cmesnding usted eaogs “The aude ws sd o eet nonizaton of 1S-yionypentaeceoi a Under ents high ton he ito ertadeine wa 8%1.3-Ditydroisthanaphthene-22 dese De Mol wt. 16821.mp, Spee ane 13S) o-oo an Rate at satan sted wt te DMPorfodase yon tn te oe PAipncmatt hayes owed yy mae Zuderunann 3% jem dros 0am ane ‘Sian 0 ye poy ny fon edt nin ete ‘Ratcyune co arene) ote ee hee po ee eae. Oe 2 Oe 22. mp i ie oe OO. oo = A Daan Sa Hh 61991.4 Oran. A Ome, Cm *W.Oppter DA. sare Bid oa 2017 1990, Asommerie reduction of tones compen és reagent (2) preparein IME by renton of equimolar moun of LAM pty ave fh, sad hav Tis eget ec symmetric econ ya ake eons ih tien enantoseleny: Redaction of lil Ketones lsscetie fe 15% fetorbezjtmetyl ketone Tht meta sh teen ps eons hat ae Inermedue im pronagladin pts”ways 2 a re Way cm 2H Ngo omo, aM iia 0, 38897, odode stag, (CH) Sip MeL Wt 31.98, bp. 170. reparation Redaction of ary alkanoa’ Th ection can be ncsompid in CHCl at ‘oom temperate nth lq of ddimetyialane eet oo nonvenist ea -astecssoue ‘indomeane (ethene ode), CH. Mo. 26738, p81", mp. 6 “Cyelopopanation radiation 0s) of Hs nthe pence of aones pies the contending csaprpane adducts wits complete fetenton of en omit. The reaction facile yicening aR subeaton: contat 0 the Simone Smt regen he econ ot wens oe tos Presse {hip metiylene CCH) the reac specs” oto Kean veayce Disbutymium 2.6-4--bay-tmetyphesoie, co. LON4CH CHIC De Me. wt 367.545 sable OF or sexe seks The reagent propre by renin of ditbutylhmioum Bye wih 2edesbwyi-tmetyipem a tlese See reduc, One rt poten in posta sie i the serene reduction ofthe Cyto rp the dese (159s Ge 104) Thisnewedusngagentishighyellestvetorthparpone Tows directo 3 wih2% stresses tod PGE, meter wont POF meet ‘ith 100% stereneectviy, The atte of 2. however, bleed wat a) eros. The eecvenes of tesetne ln pat omarion ot ‘he bly lamina een hte Uys ou were 7 Gas ‘iebuylbminam hyde (DIBA), 1, 260262; 2, 140-82 sectors, 226278;6, 198201, 7, HILT PEEL Aldoeyelzation Aihoup he cto lye Ys resto lleyhation and ora saie conto, ths Yeaton cn be sss by 2 metho ‘ria devctoped ty Raphael a Reduction fhe ee tao (ered Tom twit DIBAH producers blge keto which onized 3 th om st inne seme rete an et ea: oS ated ee esteem te oa re one, Cooma + ok tet pel Poko cea wh 7 gm196 ion nent sx are observe 11 80° (1% ld 90% yield sed on comtumed 2, ~2:1 ‘20 (99%), $01 a5 (0%; 908 rand m8- 1 a7 I: ID). “The veo ower eas temperatures tar improves the tereosletvy fhe "y Ftayana Aka D-S Kee Co Wan. OS at. il Am iim etracloopadte, 5,413.7, 14-118: 166178 Ue-Dienes Larch eal nae pepated | -enesy reaction of aii aler ‘ih tines promt by palusun clone sa itm ord emer al. Sometimes only ete mounts of Pal) are rege: eter seat ‘euite afullequvelnt Untorunsey annem of he ica cer fo "Eels ease ow foun ue uO Nowen=cn, nO Set a Sonenaens, 44-Dinetonbensbydntaming,(p-CHOC.I).CHINI, {1} Mol wt 24830, ‘mp. 166 dee The amine ca Be pepucd By reduction ofthe oxime ether, (ha) C=NOCH, with eborane 70% i)” Primary alle amines. Urine the Bony soup, the 4.4-dinethonybenz: ‘pal DMt reap isremovedby ra aid eaten eevee of spon. traschoce abe potting prowp ina fcet ses inary liye amie “Tron ant Kear” A plea! expe shown In equition (Tene of an slic act (2) wih inthe presene of eakirphersiphospinepallasim() Tes in te (Ely amine So 1% eld. Thepreteig ro removed eat ge 42% ye “Thi mt ern ne or sya (equation I) of (2 abactio 5) 8 satura cccring amino ait vated in metathesis An Imereting point i that lian of cplsheney acetate posed without < emucn,H (8 cHserencHmcr, enon om Some saa oo coon hand Chay EO. SAC Tretan hsm Bal ae Sn Dialer esos! his ypone dots not rt with moderately reseve serpin ethyl eye) bt dere with reactive symerlalen a ge dues renting tem aon of? eq othe nope with sof CO tn the rimay eeu. H abo reacts thse dems to fr ‘HotnonarenceLi other one adhe os "AP Kaho RSet, Teton Le 24 (99 Dime 1.3-scetonediaronyae (Dimetyt Sonopetate},1,270;2, 14; 4 Seti sedecling. Te ton of Saty-Ametbone-2- alles? Tee easton can be acomplsed ot formed in etna 4 Dimetylint-bbatye Doane, (CHysNC=CCOCH,Scectocactcaion of carborylicacis' Caos ais excel othe tele ton of It form sm aut a) tha rearangs to the (Zena see 2 yg phenolic amino, nd mercapto roep do wo react wth under these onions Theeter 2) earth metals of hs a of sleet a : neo? rinom 2EE+ aw cing Cr-comc, 4-Dimethlaminpyridine DMAP), 3, 18-11 §, 260 Supper: Alc, eviews A ne metho sutabe for gece preparation of DMAP (I) 6 sownimequstion( I) The relites resent 4-pyaiinopyrisin (4416) en be ‘hind inthe way by mea Stormy i place of DME o-g=d 2 ‘Thte to compounds are superior to pyridine cata for ayiation of Inycroryl groups of sero can be acetylated i yields ashigh a BO. Several usta (Cacyiatins hve been ported Tae reagnt cata the trlormation og Sei ito anlamin Ketone eqution I). Tay ae super to pyre ft “The enhanc atv of Land’ ove prin ont ert of nese ty (DMAP, pk, 9.70, Py pK. = 5.9), bas de teat in pst the foxmation of ph conenraone of Seni al, which ave ery elvan serpent. ad eat aoa a ae one ar of nad cues OF thse, pyadnepyine @) nl 3 -eeametg py “eanisie (9) are mow elective ryan; siplation, Tis aine i a efile cata for iain of yon proupe witht corde nd ethane. The method permits ae of ‘Shatter than pene, such os DM or CH,Cl, The te contin x Be ‘eto prepare uymetyy tes, Vie ae comparable oth otaned thn, 9758) frter advantage ta the elect fr eaton ‘nth primary hon! grou eens nhs Pew proce. ‘ol acto Ths amie eatalyats the eo tation of aldeyaes by scsi sn tcthlamine with movement fds Insane eis 8 of [TWP av sven i enelThs metho, homeve, pot satiny for etl teeyinon of teens. ‘Depp. These cere cam be prepared in 9-98% ye by eouping of oC prced amine aie it) Benzyl enero an achyary aby ens of DCC and extajn with tdinetylaminopyiie The ree sues een owen EE soahafe Activation of qinanes. Cnigoes ener onary ondions ea with peat stten wo ge produce o€ CC and OC coupling. Ace ets favo CC cin ene 07 OOnthe other hand -diethylaninoparitine a 2-mehonyptitie favs O—C coupling, This reaction provides reqlonpeic rote sanhones equation 1? Vs Shor: Pa = ae 1 ew Sg mt en, te, Ch i 80 08 inet -bromo-2-thoxypropenyiphcephonte (I). Mot. 27307, caller foci, ae. Greukocns, sti nembecubocni: {Ctopentneneanaltion! yi cl example fo we of 1 foe sates of ‘lpentennes tse for snl ono eytsbetanone logon econ 7 b = on wethey, me J eulleubocns, wn ey AY yn IER of tox fio ow 4 The lat erampleustes oe avatage ofthis ethos heen ete ncn fleante hyve witout efecton s ketal oupiny Aver adage hat the intramoleclar With Homer reston pesos witht oeriton he ‘ily formed eopentonne “ ° Dimi! (diromethy)phephonate,(CH0)-PCHN: D), Mol wt 184A, bp. Stem. Prepare “Alles fom dey deo eons Te ean of the alon #1 wit yt nual yroge Se thn ternal ea ne bees sete te oncton,alkyner cane obtinedin 0 as yielsomaldchdes dian! tne, Sally ay! Leone Su ot Hom all Leos, The opened mech own in equi © emorkonarsntcon+ [mt] *, eace $b Seen RS. mond ben 8,178 97) S8'Dinetiy! dibocabonate, CO¥SCH) (i) Mot. wt 1222.49. 75/10.m ‘Tae eegent canbe chan hy forangomet of may santa ih ACh fo (5, (S0% ya. feMetythicarbont eons Ketones est ith Nal ae cecal at ‘helen subsited eatbon form a-metytocatont ketone 1DNA-Dimetnlormanid, 1278-2412, 159-1543, 18554185; 8 247-202; 2, 18, 1-190, Dickorinaiion of Lewnes -Monochoination (Ch) of ally at ketones Sum acetate neat rbeaig ae (S Bours, 80-30% ik) Asay th eaton on beefed with DMF acatt a snes 80-10 in 35-85 sn BBL 'N2-Dimethyfoomamide-Dimethy| sala addt, 5,250 ‘Artalizain.The 0c (1) so an skbol convert aldehydes and a 8- mstred seb, an Ketone ito ats and eas, respect. For the ‘ont part yell ketareonly meiore (10-75%) bu eat ova ‘Carbon compound react wth Landa 2-of 13-0 to form 1-owoanesor suas, respective The Vik are oneal about 80% woh on Cf cron ne Dimethitrmamide dehy! cet, 1, 281-282; 2, 154 3, 115-115 4, 18H; 5 ‘rol acts of oxonulesides’ These derivatives of oxoncesies ate valle by team fw nls wih DM atl then wah cee ANDi tant 38h Bec at nt eeeeehet oo ae ao x Foxman fa with onnatctds becate of nai i laine mci. This ‘Exons A new met fr comeraon a's ice 10 on upeomatrted ‘tone imelvescondemtion itt DMP amet act a form acai ton, samples some yore sae . pen , ab =a wlcnmcaweny, + accretion Que Cs cmon, 2 (°Y an TEES nt Fagan siavcom mm NX-Dimthaemane dcp sea 1,285 6,22. Mean neh fa sen cet rece ol sys cv shetineniyc At eted Gyan a Theo sm weed Sin M ncopenyt an Ph ela44 Dimethyl -omahlane 3nd (1). Mol 150.20, mp. 4680 Be oS Aldehydes ‘The reagent cam sre #8 form anion equivalent, wich nme by thermola. Am exmpe ofthe we of Ifo conten of a5 ah Ie no the corzspondinghomsogous alee shown in egantion (h sam Ol Teme ie auencwosso,reneciety Uf fr reprint ete sows in ego ih sec, FB oBgy ao Dimethlecsaoninm meth, 1, 315-3185 2, 171173; 3, 25-127 4 197 19 §,280-287; 7,135.8 1196 Avommerc nthe eclprapane’ Te resco of methanol tiie with TE). 28 -oallyene-3met-- pie peryeo-L ‘Srarpine-5 ones (picks lopropane derives) nd yearns {av the ato the prods dependron he solvent and temperate Use THE $5 tinas formation 2, whereas formato lS tavored by we of DMF at 6° ‘The products and 3) can he comertd into opel pre cjeopopane- Siarbonglic ck (and sted ybutrlatones Spel jt on ee = Eeeea "7 Mpg The On (71 apo TT a NN-Dimetitpephoramie dclande \Dimehnlanidepbontant dc tee) (CH)NPOCK, Mal Wt 16136, bp. I", 907/22mm. The agent ‘ane in 96% yield bythe reaction of cibeiyne sad phar t swrifeaion? Esters ca be propsred in TBS iby he ean sci an an ale in he poses of prtine © equ) and (CH: NPOCH (1s uv) tor tempeatre. Peal eterohoxpste, CHOPOC, (87) cak ‘obe ssedasthe actatag age tea wthsomenalenpovedyilt However, ‘hrvariaton reste nmich oer ls inthe ce peri, Tein 'sappkablecven ey seo eacln wih lebas rr lobo ae converted igh yi a res reaton with at (8 hour). Ferry ales are dente ‘olen ganinhgh ye Secondary oboon econ wth gc amet ot ‘My cloves and itis. Displacement i ered it the eae of era) "dered ankle The proc ch wll the meter: ILM Wal and ADFT Sp, 7.69095 NA-Dimethytaltameyt Modi, (CH).NSOACI (Mal wt, 18359, T1471 Soper’ Alc, Eastman Pk18 Dim end reine Devsygenation The S-ysrost eoUp of numberof mets a-b-as0| yrancndes toe eed by doen it NS-Sethy alamo Seratven, Prepared ch Nat in DM nd ory renin mth alfry cri, ine, nd ‘eytuine, Toten method woe ao tong Dae The reacing agent dee, 0-2 BOG. NTs! rapes Dimety salide Teituoraaetianbyide, Reaction of eifsiden Selo ae aptly rece in amot quia yaa Tata Kai Chom, Le, 395 (1979, imethyaonom methye, 1, 14-915;2, 169-1713, 11254, 196 1978 ‘Oxienes. Ketones can be sonverted ito onianes by imety loam | neti generated min son eqton The mato parc lal forte alepepurtions a (cy,s+1cHy.s0, S cHysrenso, “Ss meee inh lorie, 1, 296-310:2, 187-1883, 1192354, 192-19; 5, 26-265 6. 395-320,7, 158-135, 8, 198-10, ‘Soler fects’ Te fie stp tl sets of 6 vetione vis the ‘esemolclar y-ailaton of the austria atone I. ade a vant of the-tolent comnts onered in the ot of Mae are tokio (0% ng KO, 1-BUOH) Homeer, ation kes he ested ‘Sour ith NSOM in DMSO-H,O mites, teat /2 being dependent onthe Sinout of water present Res reat ae otanes wah 25% aguecos DMSO (a)27.99 Actual the f-etnone s bted contain 7% fhe Teper &. Qo Po Re Ovdain? Reston of opin etratuorbort (nth DMSO at 55° wus este proact a that converted to ope (2) sion ower