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
Full Text: HTML
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. ...
Related Articles:
Pseudohalogenation of phosphites
[Shi, Enxue; Pei, Chengxin Synthesis, 2004 , # 18 p. 2995 - 2998]
Electron demand in the transition state of the cyclopropylidene to allene ring opening
[Warner, Philip; Sutherland, Robert Journal of Organic Chemistry, 1992 , vol. 57, # 23 p. 6294 - 6300]