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

Authors
TADA M MUTOH N SHIMIZU T
Citation
M. Tada et al., REACTION OF (3-FURYLMETHYL)COBALOXIME WITH DIENOPHILES - VARIABLE-MODE OF THE REACTION BY THE TYPE OF DIENOPHILES, Journal of organic chemistry, 60(3), 1995, pp. 550-553
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
60
Issue
3
Year of publication
1995
Pages
550 - 553
Database
ISI
SICI code
0022-3263(1995)60:3<550:RO(WD->2.0.ZU;2-O
Abstract
(3-Furylmethyl)cobaloxime reacts with dienophiles in three reaction mo des: (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 aromati c substitution on the furan ring with active carbonyl compounds such a s 2-oxomalonate, hexafluoroacetone, and 2-oxoaldehydes. The adducts fr om 2-aryl-2-oxoacetaldehyde easily loose the cobaloxime moiety on heat ing and give 2-(2-aryl-2-oxoacetyl)-3-methylfuran.