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

共 41 条

[1] THE DEVELOPMENT OF VERSION-3 AND VERSION-4 OF THE CAMBRIDGE STRUCTURAL DATABASE SYSTEM
ALLEN, FH
DAVIES, JE
GALLOY, JJ
JOHNSON, O
KENNARD, O
MACRAE, CF
MITCHELL, EM
MITCHELL, GF
SMITH, JM
WATSON, DG
[J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1991, 31 (02): : 187 - 204
[2] [Anonymous], 1974, INT TABLES XRAY CRYS, VIV
[3] SUBSTITUENT EFFECTS IN THE REACTION OF TRIPHENYLPHOSPHINE WITH DIAZODIPHENYLMETHANE - THE INTERPRETATION OF A U-SHAPED HAMMETT CORRELATION IN AN ELEMENTARY BIPHILIC REACTION
BETHELL, D
BOURNE, R
KASRAN, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (10): : 2081 - 2084
[4] BOCK H, 1968, ANGEW CHEM, V80, P667
[5] CHERNEGA AN, 1989, ZH OBSHCH KHIM+, V59, P1256
[6] CHERNEGA AN, 1984, ZH OBSHCH KHIM+, V54, P1979
[7] REACTION OF 3-AZIDOPROPANOL WITH TRIS(DIMETHYLAMIDO)PHOSPHORUS AND STRUCTURE OF THE PHOSPHAZIDE REACTION-PRODUCT
CHIDESTER, CG
SZMUSZKOVICZ, J
DUCHAMP, DJ
LAURIAN, LG
FREEMAN, JP
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1988, 44 : 1080 - 1083
[8] EXCHANGE-REACTIONS OF HALODIAZIRINES - SYNTHESIS OF FLUORODIAZIRINES
COX, DP
MOSS, RA
TERPINSKI, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (21) : 6513 - 6514
[9] DOMENICANO A, 1979, TETRAHEDRON LETT, V24, P2283
[10] A convenient synthesis of (S)-2-azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines
Effenberger, F
Kremser, A
Stelzer, U
[J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (02) : 607 - 618

← 1 2 3 4 5 →