Activating Agents and Protecting Groups

by Pearson, Anthony J.; Roush, William R.

• ISBN13: 9780471979272
• ISBN10: 0471979279
• Edition: 1st
• Format: Hardcover
• Copyright: 1999-07-09
• Publisher: WILEY

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.

Author Biography

Anthony J. Pearson and William R. Roush are the authors of Activating Agents and Protecting Groups, published by Wiley.

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