ALKYLIDENECARBENES FROM 1-DIAZO-1-ALKENES - THEIR ELECTROPHILICITY AND STEREOCHEMISTRY OF [2+2]-CYCLOADDITION

被引：38

作者：

GILBERT, JC

GIAMALVA, DH

机构：

[1] Department of Chemistry and Biochemistry, University of Texas, Austin

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 15期

关键词：

D O I：

10.1021/jo00041a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Determination of the rho-value for the [2 + 2]-cycloaddition of the alkylidenecarbene derived from 1-diazo-2-methyl-1-propene shows that the carbene has an electrophilicity comparable to that of the species derived from alpha-elimination of the corresponding vinyl triflate. Measurements of rho as a function of solvent indicate that the carbene is free of encumbrance with solvent molecules, at least in the sense that the latter are functioning as Lewis bases. The observed stereochemistry of the [2 + 2]-cycloaddition is consistent with the alkylidenecarbene being produced in a singlet electronic state.

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页码：4185 / 4188

页数：4

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