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Advanced Free Radical Reactions for Organic Synthesis

Advanced Free Radical Reactions for Organic Synthesis

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Published by: kaustubhvjoshi3617 on Jan 15, 2009
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07/19/2013

 
 
Advanced Free Radical Reactions for Organic Synthesis
Elsevier, 2004
Author(s): Hideo Togo 
 ISBN: 978-0-08-044374-4
Preface
, Page vii
List of Abbreviations
, Pages xi-xii
1 - What are Free Radicals?
, Pages 1-37
2 - Functional Group Conversion
, Pages 39-56
3 - Intramolecular Radical Cyclizations
, Pages 57-121
4 - Intermolecular Radical Addition Reactions
, Pages 123-156
5 - Alkylation of Aromatics
, Pages 157-170
6 - Intramolecular Hydrogen-Atom Abstraction
, Pages 171-185
7 - Synthetic Uses of Free Radicals for Nucleosides and Sugars: Barton-McCombie
 
Reaction
, Pages 187-197
8 - Barton Decarboxylation Reaction with N-Hydroxy-2-thiopyridone
, Pages 199-213
9 - Free Radical Reactions with Metal Hydrides
, Pages 215-218
10 - Stereochemistry in Free Radical Reactions
, Pages 219-230
11 - Free Radicals Related to Biology
, Pages 231-246
12 - Free Radicals for Green Chemistry
, Pages 247-256
Index
, Pages 257-258
 
 
Preface
This book covers the fundamental properties of organic free radicals and their syntheticuses. It consists of twelve chapters, starting from fundamentals and physical properties of organic free radicals, reduction and functional group conversion, cyclization, addition,alkylation onto aromatics, Barton reaction and related reactions, Barton-McCombiereaction, Barton decarboxylation, free radical reaction with metal hydrides, stereo-selective free radical reactions, free radicals in biology, and free radicals for greenchemistry. The important factors in these free radical reactions are some radical specificreactions, as mentioned in each chapter. Since the basic study on free radical reactionshas been established by Barton, Ingold, Stork, Beckwith, Giese,
etc
., free radicalreactions have become an increasingly important and attractive tool in organic synthesis,especially in the last two decades. Recently, in addition to a typical but toxic radicalreagent,
i.e.
tributyltin hydride, much less toxic but more effective radical reagents suchas tris(trimethylsilyl)silane, 1,1,2,2-tetraphenyldisilane, samarium (II) iodide, indium,
-acyloxy-2-thiopyridone, triethylborane,
etc
. have been developed. The author hopes thatthe free radical reactions will be widely applied to the synthesis of biologically attractivecompounds with high chemoselectivity and stereoselectivity, and green chemistry, basedon the advantages of free radicals.Finally, I would like to thank Dr. Adrian Shell and Mr. Derek Coleman in Elsevier Ltd.Hideo Togo
 Aug., 2003, Chiba, Japan
 
List of Abbreviations
Chemicals
AIBN
a
,
a
0
-azobis(isobutyronitrile)CAN cerium(IV) ammonium nitrateDIBAL diisobutylaluminium hydrideDMAP 4-(dimethylamino)pyridineDMSO dimethyl sulfoxideHMPA hexamethylphosphoramideLAH lithium aluminum hydrideLDA lithium diisopropylamide
m
CPBA
m
-chloroperoxybenzoic acidNBS
-bromosuccinimideNCS
-chlorosuccinimideO
2
2
·
superoxide anion radicalPCC pyridinium chlorochromatePDC pyridinium dichromatePy pyridineTBAF tetrabutylammonium uorideTEMPO 2,2,6,6-tetramethyl-1-piperidinyloxy free radical
Protecting groups
Ac acetylAr arylBn benzylBoc
tert 
-butoxycarbonylBz benzoylCbz benzyloxycarbonylEt ethyl
i
-Bu isobutyl
i
-Pr isopropylMe methyl
n-
Bu
n
-butyl
n
-Pr
n
-propylPh phenyl
s
-Bu
sec
-butyl
-Bu
tert 
-butylTBDPS
tert 
-butyldiphenylsilylTBS
tert-
butyldimethylsilylTf triuoromethanesulfonylTMS trimethylsilyl

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