Synthesis

Reliable protocol for the large scale synthesis of diphenylphosphoryl azide (DPPA)

O Wolff, SR Waldvogel

Index: Wolff, Oliver; Waldvogel, Siegfried R. Synthesis, 2004 , # 8 p. 1303 - 1305

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Citation Number: 15

Abstract

The reactivity of DPPA is based on the oxophilic nature of the phosphorous center facilitating the immediate substitution of a hydroxy moiety, whereas nonactivated alcohols are transformed only under more drastic conditions. [6] The ring-opening reaction of the epoxides with the phosphoryl azide can be realized in the presence of lithium salts. [7] In the resulting azidohydrins the alkoxy moiety is attached to the diphenylphosphoryl system representing a good leaving group. ...