9780471979272

Handbook of Reagents for Organic Synthesis : Activating Agents and Protecting Groups

by ;
  • ISBN13:

    9780471979272

  • ISBN10:

    0471979279

  • Format: Hardcover
  • Copyright: 1999-07-09
  • Publisher: WILEY
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Summary

Recognising the need for a cost effective reference work that deals not only with the most popular reagents in synthesis but also reaches the widest possible audience of practising organic chemists, the editors of 'The Encyclopedia of Reagents for Organic Synthesis' (EROS) have developed a list of the most important and useful reagents employed in the field, conveniently presented in four separate volumes. The reagents included in this volume reflect the fact that protecting groups and activation procedures are often used in combination. There are many instances in the synthesis of natural and unnatural products, pharmaceuticals, oligosaccharides, and oligonucleotides, etc., where similar tactics must be employed to prevent undesired activation or reaction of functionality. Accordingly, the most important reagents used to protect amines, alcohols, carboxyl, carbonyl and other reactive functional groups are included in this volume. The list of activating agents includes well known reagents that activate functional groups for substitution or elimination reactions, as well as less traditional examples, e.g. HMPA used to "activate" enolates and alkyllithium reagents to increase the nucleophilicity. Each article contains all of the information found in EROS as well as expanded related reagents listings and additional references to enable the reader to quickly access a broad range of information that is beyond the scope of the reagent entries themselves. This text will prove an invaluable resource.

Table of Contents

Preface ix
Introduction xi
Organic Synthesis References 1(5)
Recent Review Articles and Monographs 6(3)
Acetic Anhydride
9(7)
Acetyl Chloride (+ co-reactants)
16(10)
Aluminum Chloride
26(3)
Antimony(V) Fluoride
29(5)
Azidotris(dimethylamino)phosphonium Hexafluorophosphate
34(1)
Azobisisobutyronitrile
35(2)
Benzotriazoly-l-N-oxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP)
37(3)
0-Benzotriazolyl-N,N,N',N'-tetramethyluronium Hexafluorophosphate
40(2)
Benzoyl Chloride
42(3)
Benzyl Bromide
45(1)
Benzyl Chloroformate
46(4)
Benzyl Chloromethyl ether
50(1)
Benzyl-2,2,2-trichloroacetimidate
51(2)
2,4-Bis(4-methoxyphenyl-1,3,2,4-dithiadiphosphetane-2,4-Disulfide
53(4)
Bis(2-oxo-3-oxazolidinyl)phosphinic Chloride
57(2)
Bis(tri-N-Butyltin) Oxide
59(2)
Bis(trichloromethyl Carbonate)
61(1)
Boron Tribromide
62(4)
Boron Trichloride
66(2)
Boron Trifluorideetherate
68(9)
Bromodimethylborane
77(2)
Bromotrimethylsilane
79(2)
2-t-Butoxycarbonyloxyimino)-2-phenyl-acetonitrile
81(2)
t-Butyl Chloroformate
83(1)
t-Butyldimethylchlorosilane
84(5)
t-Butyldimethylsilyl trifluoromethanesulfonate
89(2)
t-Butyldiphenylchlorosilane
91(2)
N,N'-Carbonyldiimidazole
93(3)
Chloromethyl Methyl Ether
96(3)
2-Chloro-1-methylpyridinium Iodide
99(1)
Chlorotriethylsilane
100(2)
Chlorotriemethylsilane
102(3)
Copper(I) Trifluoromethanesulfonate
105(12)
Diazomethane
117(6)
Di-t-butyl Dicarbonate
123(7)
Di-n-butyltin Oxide
130(3)
1,3-Dicyclohexylcarbodiimide
133(3)
Diethylaluminum chloride
136(1)
N,N-Diethylaminosulfur Trifluoride (DAST)
137(3)
Diethyl Azodicarboxylate
140(4)
Diethyl Phosphorochloridate
144(3)
3,4-Dihydro-2H-pyran
147(3)
3,4-Dihydor-2H-pyrido[1,2-a]pyrimidine-2-one
150(1)
3,4-Dimethoxybenzyl bromide
151(1)
2,2-Dimethoxypropane
152(2)
Dimethylaluminum Chloride
154(2)
4-Dimethylaminopyridine
156(2)
Dimethylformamide diethyl acetal
158(3)
2,2-Dimethyl-1,3-propanediol
161(1)
Dimethyl Sulfate
162(3)
Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-proxy)-sulfirane
165(1)
Diphenylphosphinic Chloride
166(2)
Diphenyl phosphorazidate
168(2)
2,2'-Dipyridyl disulfide
170(3)
N,N'-Disuccinimidyl Carbonate
173(2)
1,2-Ethanedithiol
175(1)
2-Ethoxy-1-ethoxycarbonethoxydihydroquinoline
176(1)
Ethylaluminum Dichloride
177(5)
N-Ethylbenzisoxazolium Tetrafluoroborate
182(1)
Ethyl Chloroformate
183(3)
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide Hydrochloride
186(2)
Ethylene Glycol
188(3)
N-Ethyl-5-phenylisoxazolium-3'-sulfonate
191(3)
Ethyl Vinyl Ether
194(4)
9-FluorenylmethylChloroformate
198(3)
Hexacarbonyl Chromium
201(4)
Hexamethyldisilazane
205(2)
Hexamethylphosphoric Triamide
207(6)
Hexamethylphosphorous Triamide
213(3)
Hydrazine
216(4)
1-Hydroxybenzotriazole
220(2)
N-Hydroxypyridine-2-thione
222(3)
N-Hydroxysuccinimide
225(2)
Imidazole
227(1)
Iodomethane
228(4)
Iodonium Di-sym-collidine Perchlorate
232(2)
Iodotrimethylsilane
234(6)
Isobutene
240(3)
Isobutyl Chloroformate
243(1)
Isopropenyl Acetate
244(3)
Lithium Bromide
247(1)
Lithium Chloride
248(1)
Lithium Iodide
249(2)
Lithium Perchlorate
251(2)
Magnesium Bromide
253(2)
2-Mesitylenesulfonyl Chloride
255(2)
Methanesulfonyl Chloride
257(3)
p-Methoxybenzyl Chloride
260(3)
(Methoxycarbonylsulfamoyl)triethylammonium Hydroxide
263(2)
Methoxyethoxymethyl Chloride
265(2)
2-Methoxypropene
267(2)
Methylaluminum Dichloride
269(1)
Methyl Chloroformate
270(3)
Methyl Cyanoformate
273(3)
N-Methyl-N,N'-dicyclohexylcarbodiimidium iodide
276(1)
N-Methyl-N-nitroso-p-toluenesulfonamide, (Diazal)
277(1)
Methyl fluorosulfonate & Methyl Trifluoromethanesulfonate
278(4)
Montmorillonite K-10
282(3)
2-Morpholinoethyl Isocyanide
285(2)
o-Nitrobenzyl Alcohol
287(2)
o-Nitrophenol
289(1)
p-Nitrophenol
290(2)
Nonacarbonyldiiron
292(6)
Octacarbonyl Dicobalt
298(9)
Oxalyl Chloride
307(4)
Pentacarbonyl Iron
311(7)
Pentafluorophenol
318(4)
Phenyl Chlorothionocarbonate
322(2)
Phenyl N-Phenylphosphoramidochloridate
324(3)
Phenyl Phosphorodi(l-imidazolate)
327(1)
Phosgene
328(2)
Phosphorus(III) Bromide
330(2)
Phosphorus(V) Bromide
332(1)
Phosphorus(III) Chloride
333(2)
Phosphorus(V) Chloride
335(3)
Phosphorus(III) Iodide
338(3)
Phosphorus(V) Oxide
341(2)
Phosphorus(V) Oxide Methanesulfonic Acid
343(3)
Phosphorus Oxychloride
346(4)
p-Picolyl chloride hydrochloride
350(1)
1,3-Propanediol
350(1)
1,3-Propanedithiol
351(4)
Silver(I) Tetrafluoroborate
355(3)
Tetra-n-butylammonium Fluoride
358(3)
Tetrafluoroboric Acid
361(3)
N,N, N',N'-Tetramethylethylenediamine
364(4)
1,1'-Thiocarbonyldiimidazole
368(2)
Thionyl Chloride
370(3)
1,1'-Thionylimidazole
373(2)
2-Thiopyridyl Chloroformate
375(2)
Tin(IV) Chloride
377(6)
Titanium(IV) Chloride
383(6)
Titanium Tetraisoproxide
389(5)
p-Toluenesulfonyl Chloride
394(5)
1,2,4-Triazole
399(1)
Trichloroacetonitrile
400(2)
2,4,6-Trichlorobenzoyl Chloride
402(2)
Triethylaluminum
404(2)
Triethyl Orthoformate
406(3)
Trifluoroacetic Anhydride
409(1)
Trifluoromethanesulfonic Anhydride
410(6)
Triisopropylsilyl Chloride
416(2)
Trimethylacetyl Chloride
418(1)
Trimethyloxonium Tetrafluoroborate
419(3)
Trimethylsilyldiazomethane
422(3)
β-Trimethylsilylethanesulfonyl Chloride
425(2)
2-(Trimethylsiyl)ethoanone
427(5)
Trimethylsilyl Trifluoromethanesulfonate
432(4)
Triphenylcarbenium Tetrafluoroborate
436(2)
Triphenylphosphine-N-Bromosuccinimide
438(2)
Triphenylphosphine--Carbon Tetrabromide
440(2)
Triphenylphosphine--Carbon Tetrachloride
442(3)
Triphenylphosphine Dibromide
445(5)
Triphenylphosphine Dichloride
450(4)
Triphenylphosphine--Diethyl Azodicarboxylate
454(10)
Tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF)
464(4)
Zinc Bromide
468(3)
Zinc Chloride
471(8)
Zinc Iodide
479(2)
Zinc Bis(p-toluenesulfonate)
481(2)
List of Contributors 483(10)
Reagent Formula Index 493(4)
Subject Index 497

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