Tetrahedron p. 11441 - 11446 (1994)
Update date:2022-08-30
Topics:
Adam, Waldemar
Sauter, Markus
Benzofuran epoxides, prepared by dimethyldioxirane (DMD) oxidation of the corresponding 2,3-disubstituted benzofurans, afford on 1,2-migration the respective benzofuranones 4a,d-f, except 3-tert-butyl-2-methylbenzofuran epoxide (2c), which persists even at room temperature; however, on DMD oxidation of 2-methylbenzofuran (1b), the ester 5b is formed by a novel oxidative cleavage of the intermediary epoxide. - Key words: Dimethyldioxirane, oxidation, benzofurans, epoxides, quinone methides, benzofuranones, rearrangement
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