The reactions were examd. of ten 2,3-epoxycyclohexanones with NaH in (MeOCH2)2; the products were trapped by treatment with Me3CSiMe2Cl and Et3N. Generally, the main reaction products were the corresponding silylated phenols. E.g., carvone epoxide gave 66% 3,4-Me3CSiMe2O(Me)C6H3CMe:CH2. This aromatization proceeds by deprotonation at the α'-C atom followed by O-silylation, β'-proton removal, olefinic bond shift, oxirane ring cleavage, and 1,2-elimination.
Base-promoted rearrangement of 2,3-epoxycyclohexanones to phenols / Bellesia, Franco; Ghelfi, Franco; Grandi, Romano; Pagnoni, Ugo Maria. - In: JOURNAL OF CHEMICAL RESEARCH. SYNOPSES. - ISSN 0308-2342. - STAMPA. - /:(1985), pp. 400-401.
Base-promoted rearrangement of 2,3-epoxycyclohexanones to phenols
BELLESIA, Franco;GHELFI, Franco;GRANDI, Romano;PAGNONI, Ugo Maria
1985
Abstract
The reactions were examd. of ten 2,3-epoxycyclohexanones with NaH in (MeOCH2)2; the products were trapped by treatment with Me3CSiMe2Cl and Et3N. Generally, the main reaction products were the corresponding silylated phenols. E.g., carvone epoxide gave 66% 3,4-Me3CSiMe2O(Me)C6H3CMe:CH2. This aromatization proceeds by deprotonation at the α'-C atom followed by O-silylation, β'-proton removal, olefinic bond shift, oxirane ring cleavage, and 1,2-elimination.
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