ALPHA-DIKETONES IN [4- REACTIONS OF DIMETHYL 2,3-DIOXOSUCCINATE WITH ENOL ETHERS(2] CYCLOADDITIONS )

Authors
SUSTMANN R FELDERHOFF M
Citation
R. Sustmann et M. Felderhoff, ALPHA-DIKETONES IN [4- REACTIONS OF DIMETHYL 2,3-DIOXOSUCCINATE WITH ENOL ETHERS(2] CYCLOADDITIONS ), Heterocycles, 40(2), 1995, pp. 1027-1034
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
40
Issue
2
Year of publication
1995
Pages
1027 - 1034
Database
ISI
SICI code
0385-5414(1995)40:2<1027:AI[ROD>2.0.ZU;2-J
Abstract
Dimethyl 2,3-dioxosuccinate (1) undergoes cycloaddition with enol ethe rs. Dihydrodioxine derivates, products of [4+2] cycloaddition, are for med with tetraethoxyethylene and E-1,2-dimethoxyethyiene. The stereosp ecificity of the reaction of 1 with E-1,2-dimethoxyethylene suggests a concerted mechanism for this cycloaddition. The polarized double bond of ethyl vinyl ether reacts with 1 to give ydro-2,3-dimethoxycarbonyl -2,3-epoxy-5-ethoxyfuran in a hitherto unknown reaction of 1,2-diketon es.