F. Toda, Y. Takehira
Jun 1, 1972
Citations
0
Influential Citations
4
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The reactions of 2-bromo-3,4-bis(diphenylmethylene)cyclobutanone (III) with methanolic and 2-propanolic potassium hydroxide afforded methyl 4-methoxy-2,3-bis(diphenylmethylene)butyrate (VIII) and 3,4-bis-(diphenylmethylene)-γ-lactone (XXI) respectively. The reaction of the 2,2-dibromo analog of III (XXV) with methanolic potassium hydroxide afforded methyl 4-methoxy-4-bromo-2,3-bis(diphenylmethylene)butyrate (XXVIIIa) and methyl 4,4-diphenyl-3-formyl-2-diphenylmethylenebut-3-enate (XXIIIa) in approximately equal yields. However, the reaction of XXV with 2-propanolic potassium hydroxide afforded XXIIIc exclusively. The reaction mechanism was disclosed to be that the haloester intermediates V and XXVII initially formed from III and XXV respectively, by the addition of alcohol to the carbonyl followed by the ring-opening, react with the alkoxy and hydroxy anions competitively.