1,2-Vinyl and 1,2-acetylenyl migration in Rh(II) carbene reaction: Remarkable bystander effect

被引：58

作者：

Shi, WF ^{[1
]}

Xiao, FP ^{[1
]}

Wang, JB ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 11期

关键词：

D O I：

10.1021/jo050173c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds have been synthesized, and their Rh(II)-catalyzed reaction was investigated. 1,2-Migration was the predominant reaction pathway, and the migratory aptitude was found to be dramatically affected by the beta-substituents. The 1,2-vinyl and 1,2-acetylenyl group migration occurs preferentially in the presence of beta-hydrogen in Rh-2(OAc)(4)-catalyzed reaction of beta-(trichloroacetyl)amino alpha-diazo carbonyl compounds. A possible reaction mechanism is discussed.

引用

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页码：4318 / 4322

页数：5

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