ALTERNATIVES TO ALPHA-DIAZO KETONES FOR TANDEM CYCLIZATION CYCLOADDITION AND CARBENOID ALKYNE METATHESIS STRATEGIES - NOVEL CYCLIC ENOL ETHER FORMATION VIA CARBONYL YLIDE REARRANGEMENT REACTIONS

被引：28

作者：

FAIRFAX, DJ ^{[1
]}

AUSTIN, DJ ^{[1
]}

XU, SL ^{[1
]}

PADWA, A ^{[1
]}

机构：

[1] EMORY UNIV, DEPT CHEM, ATLANTA, GA 30322 USA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 21期

关键词：

D O I：

10.1039/p19920002837

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Attempts to form carbonyl ylides from free carbenes derived from diazirines or diazo compounds lacking electron-withdrawing substituents resulted in azine formation or Wolff rearrangement, respectively. Iodonium ylides proved to be a possible alternative to alpha-diazo compounds for metallocarbenoid generation, similar reactivity being observed for both systems. Studies into the rearrangement chemistry of carbonyl ylides provided a novel cyclic enol-ether synthesis via a 1,4-hydrogen shift process.

引用

页码：2837 / 2844

页数：8

共 64 条

[1] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].