Some important abbreviations for the OC-II lecture

Alkyl groups

CH3 Me (Methyl) or Me or CH3

C2H5 Et (Ethyl)

C3H7 Pr (Propyl) n-Propyl: nPr Isopropyl: iPr

C4H9 Bu (Butyl)

nBu iBu sBu tBu (tert-Butyl)

C5H11 (Pent (Pentyl

/ Am) or Amyl)

nPent / nC5H11 iAm (Isoamyl) tAm / tPent Np (Neopentyl)

c-C6H11 Cy (Cyclohexyl)

n = normal; i = iso; s = sec; t = tert; c = cyclo; short forms are written as: iPr or i-Pr or iPr or iPr ...

Amyl and Pentyl can be used synonymous ; "Amyl" without further details mostly means Isopentyl (= iso-Amyl); "Pentyl"
without further details often means n-Pentyl, "Neopentyl" is the only important name for that group (not: "Neoamyl").
Higher alkyls may be abbreviated (Hex, Hept, Oct, Non, Dec), but use of the sum formula is more clear: n-C6H13, n-C7H15 etc.

Important substituents
Me

Me Me

Me
Ph = Phenyl [C6H5] Bn = Benzyl [C7H7] pTol = para-Tolyl [C7H7] Mes = Mesityl All = Allyl

O O O O O
S Me S Me S CF3
Me
O O O

Bz = Benzoyl Ac = Acetyl [C2H3O] Ts or: pTs = Tosyl Ms = Mesyl Tf = Triflyl

[C7H5O] AcO / OAc = Acetate (p-Toluenesulfonyl) (Methanesulfonyl) (Trifluoromethanesulfonyl)
-OTs = Tosylate -OMs = Mesylate TfO- / -OTf = Triflate

Protecting groups

Carbamate protecting groups for amines: Silyl protecting groups for alcohols:

Boc O Me
TMS or Me3Si
(tert-Butyloxycarbonyl) O Si Me
(Trimethylsilyl)
Me
Cbz or Z O
Me
(Benzyloxycarbonyl) TBS or TBDS or TBDMS
O Si
O (tert-Butyldimethylsilyl) Me
Fmoc
O
(Fluorenylmethyloxycarbonyl) Ph
TBPS or TBDPS
Si
Ph (tert-Butyldiphenylsilyl) Ph
Ether protecting groups Tr = Trityl
for alcohols: Ph
(Triphenylmethyl)
Ph
 Functional substituents or particels (generic group abbreviations)

Nu / Nuc Nucleophile X, Y, Z electronegative groups/substituents

E+ Electrophile Z π-acceptors [often including σ-acceptors]
LA Lewis acid X σ-acceptors > π-donors (often: halogens)

B Base R any kind of carbon-based residue; alkyl group

M Metal (not: Me) Ar Aryl = aromatic residue (bound via C(sp2) carbon)
E -CO2R, "Ester" (not often used)

Reagents

Me Me
N N
N
N N N
N
H H N
N

Py DMAP Im TMP iPr2NEt DBU

(Pyridine) (4-Dimethylamino- (Imidazole) (2,2,6,6-Tetra- (Hünig base) (1,8-Diazabicyclo[5.4.0]-
pyridine) methylpiperidine) undec-7-ene)

O O•
Me O O
Cl N N
OOH O N O N
O Br Cl

MCPBA od. mCPBA NMO NBS NCS TEMPO

(meta-Chloroperbenzoic (N-Methylmor- (N-Bromo- (N-Chloro- (Tetramethyl-
acid) pholine-N-oxide) succinimide) succinimide) piperidyloxyl)

Me3Si SiMe3 NMe2

N EtO2C N N C N Me2N
N CO2Et
H
HMDS DEAD DCC TMEDA
(Hexamethyldisilazane) (Diethylazodicarboxylate) (Dicyclohexylcarbodiimide) (N,N,N',N'-Tetramethyl-
ethylenediamine)

Solvents

O O O
S Me Cl Cl Cl
Me Me H N Me C N Cl
Me
DMSO DMF MeCN Me2CO DCM DCE
(Dimethylsulfoxide, (N,N-Dimethyl- (Acetonitrile) (Acetone) (Dichloro- (1,2-Dichloro-
or: methyl sulfoxide) formamide) methane) ethane)

O O
O S O OMe HO
N MeO
O
Me

NMP Sulfolane THF Et2O DME or Glyme tBuOH

(N-Methyl-2-pyrrolidone) (Tetrahydrofurane) (Diethylether, (1,2-Dimethoxyethane) (tert-Butanol)
ethyl ether)

Me O
PhH or C6H6 PhMe or C6H5Me EtOAc
(Benzene) (Toluene) (Ethyl acetate) OEt

L. Hintermann 1.3.2.2016