Unexpected Staudinger reaction of alpha-azidoacetonitriles alpha-phenyl substituted with triphenylphosphine. Preparation, X-ray crystal and molecular structures of a phosphazine, an aminophosphonium carbanion salt and a phosphazide, with (Z)-configuration

被引：50

作者：

Molina, P ^{[1
]}

LopezLeonardo, C ^{[1
]}

LlamasBotia, J ^{[1
]}

FocesFoces, C ^{[1
]}

FernandezCastano, C ^{[1
]}

机构：

[1] CSIC,INST QUIM FIS ROCASOLANO,DEPT CRISTALOG,E-28006 MADRID,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 28期

关键词：

D O I：

10.1016/0040-4020(96)00499-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Staudinger reaction of alpha-azidophenylacetonitrile with triphenylphosphine in 1:2 molar ratio provides the triphenylphosphazine 4 derived from alpha-diazophenylacetonitrile, whereas in 2:1 molar ratio the final product is found to be the aminotriphenylphosphonium salt of phenylmalononitrile 6. However, the Staudinger reaction of alpha-azidodiphenylacetonitrile with triphenylphosphine affords the corresponding (Z)-phosphazide 17. The crystal and molecular structures of compounds 4, 6, and 17 have been determined by X-ray analysis. Compound 17 is the first isolated phosphazide which presents the (Z)-configuration with respect to the central N-N bond of the PN3C moiety (P-N-N-N=0.0(3)degrees). Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9629 / 9642

页数：14

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