Protective Groups in Organic Synthesis, 3rd Edition

by ;
Edition: 3rd
Format: Hardcover
Pub. Date: 1999-04-01
Publisher(s): Wiley-Interscience
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Summary

From the reviews of the previous editions:* "For completeness, the authors . . . include protective groups and techniques for formation and cleavage that are seldom used as well as those that are more common. . . . Anyone who does organic synthesis must have convenient access to this book." -Journal of the American Chemical Society.* "Essential to the modern synthetic organic chemist . . . should be in the libraries of all academic, governmental, and industrial organizations concerned with organic synthesis." -Polymer News.Reflecting the latest advances in protective group methodology, this Third Edition of the proven laboratory reference is expanded by more than 50%, providing readers with a comprehensive compendium of 1,050 of the most useful protective groups as well as 5,350 references to original publications. Protective groups are organized by six major organic functional groups: hydroxyl, amino, carboxyl, carbonyl, sulfhydryl, and phosphate groups (the last new to this edition). Also added in this edition are protection of the alkyne-CH, expanded coverage of protection of all groups, and many new enzymatic methods of protection and deprotection. Each chapter briefly describes the classes of available protective groups, followed by an in-depth look at the chemistry of individual protective groups, their properties, and the best methods of formation and cleavage. Ten reactivity charts with more than 28,000 entries summarize the relative reactivities of 270 commonly used protective groups with 108 reagents. This book will be an indispensable reference for synthetic chemists and students.

Author Biography

THEODORA W. GREENE, PhD, is Assistant Editor for Organic Syntheses and the former librarian for the Rowland Institute for Science. She holds a PhD in Chemistry from Harvard University.<br> <br> G. M. WUTS, PhD, is Senior Scientist at Pharmacia & Upjohn in Kalamazoo, Michigan and has a PhD in Chemistry from Northwestern University.

Table of Contents

Abbreviations xiii
The Role of Protective Groups in Organic Synthesis
1(16)
Protection for the Hydroxyl Group, Including 1,2- and 1, 3-Diols
17(229)
Ethers
23(126)
Esters
149(52)
Protection for 1,2- and 1,3-Diols
201(45)
Protection for Phenols and Catechols
246(47)
Protection for Phenols
249(38)
Ethers
249(27)
Esters
276(11)
Protection for Catechols
287(6)
Cyclic Acetals and Ketals
287(3)
Cyclic Esters
290(3)
Protection for the Carbonyl Group
293(76)
Acetals and Ketals
297(51)
Miscellaneous Derivatives
348(16)
Monoprotection of Dicarbonyl Compounds
364(5)
Protection for the Carboxyl Group
369(85)
Esters
373(69)
Amides and Hydrazides
442(12)
Protection for the Thiol Group
454(40)
Thioethers
457(25)
Thioesters
482(5)
Miscellaneous Derivatives
487(7)
Protection for the Amino Group
494(160)
Carbamates
503(47)
Amides
550(23)
Special--NH Protective Groups
573(42)
Protection for Imidazoles, Pyrroles, and Indoles
615(17)
Protection for Amides
632(22)
Protection for the Alkyne--CH
654(6)
Protection for the Phosphate Group
660(41)
Reactivities, Reagents, and Reactivity Charts
701(48)
Reactivities
701(1)
Reagents
702(3)
Reactivity Charts
705(44)
Protection for the Hydroxyl Group: Ethers
708(4)
Protection for the Hydroxyl Group: Esters
712(4)
Protection for 1,2- and 1,3-Diols
716(4)
Protection for Phenols and Catechols
720(4)
Protection for the Carbonyl Group
724(4)
Protection for the Carboxyl Group
728(4)
Protection for the Thiol Group
732(4)
Protection for the Amino Group: Carbamates
736(4)
Protection for the Amino Group: Amides
740(4)
Protection for the Amino Group: Special--NH Protective Groups
744(5)
Index 749

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