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Protective groups in organic synthesis 4ed by Greene & Wuts (2007)

The Fourth Edition of Greene's Protective Groups in Organic Synthesis continues to be an indispensable reference for controlling the reactivity of the most common functional groups during a synthetic sequence. This new edition incorporates the significant developments in the field since publication of the third edition in 1998, including...

* New protective groups such as the fluorous family and the uniquely removable 2-methoxybenzenesulfonyl group for the protection of amines

* New techniques for the formation and cleavage of existing protective groups, with examples to illustrate each new technique

* Expanded coverage of the unexpected side reactions that occur with protective groups

* New chart covering the selective deprotection of silyl ethers

* 3,100 new references from the professional literature

The content is organized around the functional group to be protected, and ranges from the simplest to the most complex and highly specialized protective groups.

Content

Preface to the Fourth Edition.

Preface to the Third Edition.

Preface to the Second Edition.

Preface to the First Edition.

Abbreviations.

1. The Role of Protective Groups in Organic Synthesis.

2. Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols.

Ethers.

Esters.

Protection for 1,2- and 1,3-Diols.

3. Protection for Phenols and Catechols.

Protection for Phenols.

Ethers.

Silyl Ethers.

Esters.

Carbonates.

Aryl Carbamates.

Phosphinates.

Sulfonates.

Protection for Catechols.

Cyclic Acetals and Ketals.

Cyclic Esters.

Protection for 2-Hydroxybenzenethiols.

4. Protection for the Carbonyl Group.

Acetals and Ketals.

Miscellaneous Derivatives.

Monoprotection of Dicarbonyl Compounds.

5. Protection for the Carboxyl Group.

Esters.

Amides and Hydrazides.

Protection of Boronic Acids.

Protection of Sulfonic Acids.

6. Protection for the Thiol Group.

Thioethers.

Thioesters.

Miscellaneous Derivatives.

7. Protection for the Amino Group.

Carbamates.

Amides.

Special —NH Protective Groups.

Protection for Imidazoles, Pyrroles, Indoles, and other Aromatic Heterocycles.

Protection for the Amide —NH.

Protection for the Sulfonamide —NH.

8. Protection for the Alkyne —CH.

9. Protection for the Phosphate Group.

Some General Methods for Phosphate Ester Formation.

Removal of Protective Groups from Phosphorus.

Alkyl Phosphates.

Phosphates Cleaved by Cyclodeesterifi cation.

Benzyl Phosphates.

Phenyl Phosphates.

Photochemically Cleaved Phosphate Protective Groups.

Amidates.

Miscellaneous Derivatives.

10. Reactivities, Reagents, and Reactivity Charts.

Reactivities.

Reagents.

Reactivity Charts.

1 Protection for the Hydroxyl Group: Ethers.

2 Protection for the Hydroxyl Group: Esters.

3 Protection for 1,2- and 1,3-Diols.

4 Protection for Phenols and Catechols.

5 Protection for the Carbonyl Group.

6 Protection for the Carboxyl Group.

7 Protection for the Thiol Group.

8 Protection for the Amino Group: Carbamates.

9 Protection for the Amino Group: Amides.

10 Protection for the Amino Group: Special —NH Protective Groups.

11 Selective Deprotection of Silyl Ethers.

Index.

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Below see the 3 edition of the same work:

Protective groups in organic synthesis 3rd by Greene & Wuts (2007)

Publisher: Wiley-Interscience; 3 edition (May 15, 1999) | ISBN: 0471160199 | Pages: 816 | PDF | 8 MB

Description

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.

Editorial Review

I rate "Protective Groups in Organic Synthesis" as very successful: On the one hand the book combines a vast number of functional groups and their protection groups with different methods for protecting and deprotecting, on the other hand stability data to a variety of protection groups are summarized in tabular form. The methods were presented in a short form, which are supplemented with appropriate references.

The present book is very comprehensive, and one will meet very rarely a synthesis problem to which no solution, in form of a of protection group, is present. For this reason, this book should be present in any synthesis laboratory.

Contents

The Role of Protective Groups in Organic Synthesis.

Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols.

Protection for Phenols and Catechols.

Protection for the Carbonyl Group.

Protection for the Carboxyl Group.

Protection for the Thiol Group.

Protection for the Amino Group.

Protection for the Alkyne-CH.

Protection for the Phosphate Group.

Reactivities, Reagents, and Reactivity Charts.

Rating:
2.5 out of 5 by Book123