Checked by Christina Bodurow and M. F. Semmelhack.
1. Procedure
2. Notes
3. Discussion
The procedure described is essentially that of Shioiri and Yamada.
4 Diphenyl phosphorazidate is a useful and versatile reagent in organic synthesis.
5 6 It has been used for racemization-free peptide syntheses,
4,7,8 thiol ester synthesis,
9 a modified Curtius reaction,
7,10,11 C-acylation of active methylene compounds,
12 esterification of an α-substituted carboxylic acid,
13 formation of diketopiperazines,
14 an alkyl azide synthesis,
15 phosphorylation of alcohols and amines,
16 and polymerization of amino acids and peptides.
17 Furthermore,
diphenyl phosphorazidate acts as a nitrene source
3 and as a 1,3-dipole.
18,19 An example of the ring contraction of cyclic ketones to form cycloalkanecarboxylic acids is presented on page 135 in this volume.
Copyright © 1921-2002, Organic Syntheses, Inc. All Rights Reserved