Tetrahedron

Photolysis of some unsymmetrical phosphinic azides in methanol: Relative migratory aptitudes of alkyl groups and phenyl in the curtius-like rearrangement

MJP Harger, S Westlake

Index: Harger, Martin J. P.; Westlake, Sally Tetrahedron, 1982 , vol. 38, # 20 p. 3073 - 3078

Full Text: HTML

Citation Number: 19

Abstract

When an alkylphenylphosphinic acid PRhP (O) N3 (R= Me, Et, Pri, or But) is photolysed in MeOH either the alkyl or phenyl group can migrate from P to N in the Curtius-like rearrangement. The composition of the product shows that migration of the alkyl group R is preferred. However, the preference is not great and decreases as R changes But→ Pri→ Et→ Me (approx. migratory aptitudes relative to Ph: 2.1, 1.7, 1.3 and 1.2 respectively), ...