Acid-catalyzed Rearrangement of 3-Alkyl-3-phenylglycidic Ester
1976 年 40 巻 8 号 p. 1547-1549
詳細
1976 年 40 巻 8 号 p. 1547-1549
The acid-catalyzed rearrangement of 3-alkyl-3-phenylglycidic esters with ethyl, propyl or isopropyl substituents at 3-position (Ib, Ic and Id) gave substituted 2-hydroxy-3-butenoic esters (IIb, IIc and IId) and substituted pyruvic esters (IIIb, IIIc and IIId). The mechanism of their formation is thought to be the ring cleavage of the oxirane followed by competition of proton elimination at 4-position with hydride shift at 2-position. Prolonged treatment of IId gave a dienoic ester (IV) resulting from dehydration, whereas the same treatment of IIb and IIc gave the unchanged starting materials.
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