REARRANGEMENT OF 2,3-DISUBSTITUTED BENZOFURAN EPOXIDES PREPARED BY DIMETHYLDIOXIRANE OXIDATION

Authors
ADAM W SAUTER M
Citation
W. Adam et M. Sauter, REARRANGEMENT OF 2,3-DISUBSTITUTED BENZOFURAN EPOXIDES PREPARED BY DIMETHYLDIOXIRANE OXIDATION, Tetrahedron, 50(39), 1994, pp. 11441-11446
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
39
Year of publication
1994
Pages
11441 - 11446
Database
ISI
SICI code
0040-4020(1994)50:39<11441:RO2BEP>2.0.ZU;2-X
Abstract
Benzofuran epoxides, prepared by dimethyldioxirane (DMD) oxidation of the corresponding 2,3-disubstituted benzofurans, afford on 1,2 migrati on the respective benzofuranones 4a,d-f, except 3-tert-butyl-2-methylb enzofuran epoxide (2c), which persists even at room temperature; howev er, on DMD oxidation of 2-methylbenzofuran (1b), the ester 5b is forme d by a novel oxidative cleavage of the intermediary epo;dde.