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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