DECOMPOSITION OF 2-DIAZO-1,3-DIKETONES - STEREOCONTROL OF THE MECHANISM

被引：15

作者：

NIKOLAEV, VA

POPIK, VV

机构：

[1] Department of Organic Chemistry, Institute of Chemistry St.Petersburg State University, St. Petersburg

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 31期

关键词：

D O I：

10.1016/S0040-4039(00)60116-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Complete ''inversion'' of alkyl to aryl migratory tendency in Wolff rearrangement of diazodiketones with Z,Z-conformation was revealed by comparing decomposition behavior of the planar diazo tetralindione with its twisted acyclic analogues. Dramatic change in regioselectivity of this process was accompanied by the appearance of X-H insertion products in the reaction mixture. These data suggest that on the way from planar cyclic to highly skewed acyclic aroylacyldiazomethanes concerted Wolff rearrangement turns into a carbenic process.

引用

页码：4483 / 4486

页数：4

共 9 条

[1]

HAYES G, 1973, J CHEM SOC P1, P1206

[2] MECHANISTIC STUDIES ON THE WOLFF REARRANGEMENT - THE CHEMISTRY AND SPECTROSCOPY OF SOME ALPHA-KETOCARBENES [J].