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Dioxirane Epoxidation of α,β‐Unsaturated Ketones
Author(s) -
Adam Waldemar,
Hadjiarapoglou Lazaros,
Smerz Alex
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240134
Subject(s) - dioxirane , dimethyldioxirane , chemistry , acetone , ketone , organic chemistry , medicinal chemistry
The synthesis of epoxides 3a – r is achieved in excellent yields by reaction of the α,β‐unsaturated ketones 1a – c , 4,4′‐disubstituted ( E )‐chalcones 1d – o , and 2′‐hydroxy‐4‐substituted ( E )‐chalcones 1p – r with isolated dimethyldioxirane ( 2a ) (as acetone solution) and/or in situ generated ethyl(methyl)dioxirane ( 2b ). This method constitutes a useful alternative to the Weitz‐Scheffer epoxidation (alkaline H 2 O 2 ) of such electronpoor substrates.