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
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.
引用
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页码:550 / 553
页数:4
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