Reactivity charts

The reactivities in the charts refer only to the protected functionality, not to atoms adjacent to the functional group for example, RCOOEt L (low) 

LiN-Z-Pr /Mel and 105 K2C03/MeI] were added after some of the charts had been completed reactivities to these reagents are not included for all charts. 

The number used to designate a protective group (PG) in a Reactivity Chart is the same as that used in the body of the text in the first edition. 

Protective group numbers in the Reactivity Charts are not continuous, since not all of the protective groups described in the text are included in the charts. The protective groups that are included in the Reactivity Charts are in general those that have been used most widely consequently, considerable experimental information is available for them. 

The Reactivity Charts were prepared in collaboration with the following chemists, to whom we are most grateful John O. Albright, Dale L. Boger, Dr. Daniel J. Brunelle, Dr. David A. Clark, Dr. Jagabandhu Das, Herbert Estreicher, Anthony L. Feliu, Dr. Frank W. Hobbs, Jr., Paul B. Hopkins, Dr. Spencer Knapp, Dr. Pierre Lavallee, John Munroe, Jay W. Ponder, Marcus A. Tius, Dr. David R. Williams, and Robert E. Wolf, Jr. 

Glycol and Cf-hydroxy acid cleavage Oxidative decarboxylation Oxidative rearrangement of olefins 

Some Cope rearrangements and Cope eliminations Claisen or Cope rearrangement Ester cracking Conia ene reaction 

One requirement of a protective group is stability to a given reaction. The charts that follow were prepared as a guide to relative reactivities and thereby as an aid in the choice of a protective group. The reactivities in the charts were estimated 

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Ethers are among the most used protective groups in organic synthesis. They vary from the simplest, most robust, methyl ether to the more elaborate, substituted, trityl ethers developed for use in nucleotide synthesis. They are formed and removed under a wide variety of conditions. Some of the ethers that have been used to protect alcohols are included in Reactivity Chart 1. ... 

Some of the protective groups for diols are listed in Reactivity Chart 3. 

Some of the more important phenol and catechol protective groups are included in Reactivity Chart 4. ... 

Derivatives of carbonyl compounds that have been used as protective groups in synthetic schemes are described in this chapter some of the more important protective groups are listed in Reactivity Chart 5. ... 

Thiol esters, which are more reactive to nucleophiles than are the corresponding oxygen esters, have been prepared to activate carboxyl groups for both lactoniza-tion and peptide bond formation. For lactonization S-f-butyl and S-2-pyridyP esters are widely used. Some methods used to prepare thiol esters are shown below. The S-r-butyl ester is included in Reactivity Chart 6. 

Some amides and hydrazides that have been prepared to protect carboxyl groups are included in Reactivity Chart 6. 

In this chapter detailed information is pn vided for the more useful protective groups (some of which are included in Reactivity Charts 8-10) structures and references are given for protective groups that seem to have more limited use. ... 

These 108 reagents are used in the Reactivity Charts that have been prepared for each class of protective groups. The reagents and some of their properties are described on the following pages. 

Reactivity Chart 1. Protection for the Hydroxyl Group Ethers... 

Reactivity Chart 2. Protection for the Hydroxyi Group Esters... 

Reactivity Chart 4. Protection for Phenois and Catechols (Continued)... 

Reactivity Chart 6. Protection for the Carboxyl Group (ContlnuBd)... 

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