SYNTHESIS OF A 2H-AZIRINE BY [1+2]-CYCLOADDITION OF A PHOSPHINOCARBENE WITH A NITRILE AND ITS RING-EXPANSION TO A 1,2-LAMBDA(5)-AZAPHOSPHETE

被引：50

作者：

ALCARAZ, G ^{[1
]}

WECKER, U ^{[1
]}

BACEIREDO, A ^{[1
]}

DAHAN, F ^{[1
]}

BERTRAND, G ^{[1
]}

机构：

[1] CNRS,CHIM COORDINAT LAB,F-31077 TOULOUSE,FRANCE

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 11期

关键词：

CARBENES; CYCLOADDITIONS; HETEROCYCLES; PHOSPHORUS COMPOUNDS;

D O I：

10.1002/anie.199512461

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new type of carbene reaction is observed with the stable phosphinocarbene 1. It reacts with benzonitrile to give the 2H‐azirine 2, which in dichloromethane is converted into the 1,2λ5‐azaphosphete 3 after addition of a catalytic amount of dichloro(p‐cymene)ruthenium(II). R = (c‐C6H11)2N. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany

引用

收藏

页码：1246 / 1248

页数：3

相关论文

共 39 条

[1] SYNTHESIS AND EVOLUTION OF PHOSPHANYLCARBENE BORANE ADDUCTS [J].

ALCARAZ, G ;

REED, R ;

BACEIREDO, A ;

BERTRAND, G .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (17) :1354-1355

[2] ELECTRON-DISTRIBUTION IN A STABLE CARBENE [J].

ARDUENGO, AJ ;

DIAS, HVR ;

DIXON, DA ;

HARLOW, RL ;

KLOOSTER, WT ;

KOETZLE, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6812-6822

[3] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[4] CHEMICAL SHIELDING TENSER OF A CARBENE [J].

ARDUENGO, AJ ;

DIXON, DA ;

KUMASHIRO, KK ;

LEE, C ;

POWER, WP ;

ZILM, KW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6361-6367

[5] PHOTOELECTRON-SPECTROSCOPY OF A CARBENE/SILYLENE/GERMYLENE SERIES [J].

ARDUENGO, AJ ;

BOCK, H ;

CHEN, H ;

DENK, M ;

DIXON, DA ;

GREEN, JC ;

HERRMANN, WA ;

JONES, NL ;

WAGNER, M ;

WEST, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6641-6649

[6]

ARDUENGO AJ, 1992, J AM CHEM SOC, V114, P4430

[7] ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].

BENNETT, MA ;

SMITH, AK .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241

[8] SYNTHESIS AND REACTIVITY OF CYCLIC 6-MEMBERED 6-PI-MEMBERED AND 4-MEMBERED 4-PI-ELECTRON YLIDES [J].

BIEGER, K ;

TEJEDA, J ;

REAU, R ;

DAHAN, F ;

BERTRAND, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8087-8094

[9] DEFORMATION DENSITY OF A DIAZIRINE RING IN THE X-RAY STRUCTURE OF 3-[(PARA-NITROPHENOXY)METHYL]-3-CHLORODIAZIRINE [J].

CAMERON, TS ;

BAKSHI, PK ;

BORECKA, B ;

LIU, MTH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1889-1890

[10] PREPARATION OF STABLE DIVALENT SPECIES RAISES ISSUES OF ELECTRONIC-STRUCTURE [J].

DAGANI, R .

CHEMICAL & ENGINEERING NEWS, 1994, 72 (18) :20-22

← 1 2 3 4 →