REACTION OF (3-FURYLMETHYL)COBALOXIME WITH DIENOPHILES - VARIABLE-MODE OF THE REACTION BY THE TYPE OF DIENOPHILES

被引：18

作者：

TADA, M

MUTOH, N

SHIMIZU, T

机构：

[1] The Department of Chemistry, School of Science and Engineering, Waseda University, Okubo, Shinjukuku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 03期

关键词：

D O I：

10.1021/jo00108a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(3-Furylmethyl)cobaloxime reacts with dienophiles in three reaction modes: (a) a 1,4-addition with N-phenylmaleimide and maleic anhydride, (b) a 1,4-cycloaddition and concomitant 1,3-migration of the cobaloxime moiety with dimethyl acetylenedicarboxylate, and (c) a formal aromatic substitution on the furan ring with active carbonyl compounds such as 2-oxomalonate, hexafluoroacetone, and 2-oxoaldehydes. The adducts from 2-aryl-2-oxoacetaldehyde easily loose the cobaloxime moiety on heating and give 2-(2-aryl-2-oxoacetyl)-3-methylfuran.

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页码：550 / 553

页数：4

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