SYNTHESIS AND REACTIVITY OF CYCLIC 6-MEMBERED 6-PI-MEMBERED AND 4-MEMBERED 4-PI-ELECTRON YLIDES

被引：42

作者：

BIEGER, K ^{[1
]}

TEJEDA, J ^{[1
]}

REAU, R ^{[1
]}

DAHAN, F ^{[1
]}

BERTRAND, G ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1994年 / 116卷 / 18期

关键词：

D O I：

10.1021/ja00097a015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Phosphinonitrilimine 1 and phosphine azides 4 react with dimethyl acetylenedicarboxylate via formal [4 + 2] cycloadditions affording 1,2,3 lambda(5)-diazaphosphinine 2 (90% yield) and 1,2,3,4 lambda(5)-triazaphosphinines 5 (63-75% yield), respectively. Although 2 is reluctant toward dinitrogen extrusion, derivatives 5 afford 1,2 lambda(5)-azaphosphetes 6 (80-90% yield) by heating in refluxing toluene. Four-pi-electron four-membered rings 6 react via the ring nitrogen atom with a variety of electrophiles. The four-membered ring structure is preserved by addition of boron trifluoride or iodomethane, while ring-opening reactions are observed with water, pentafluorobenzonitrile, and carbon disulfide; ring expansion reactions occurred with dimethyl acetylenedicarboxylate, methyl isothiocyanate, phenyl isocyanate, trimethylsilyl isocyanate, and isothiocyanate.

引用

页码：8087 / 8094

页数：8

共 61 条

[1] THE SYNTHESIS OF UNUSUAL ORGANIC-MOLECULES FROM AZOALKANES [J].