Methylene Analogs of Cyclobutenedione. III. The Reaction of 2-Bromo- and 2,2-Dibromo-3,4-bis(diphenylmethylene)cyclobutanone with Alcoholic Potassium Hydroxide

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概要

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• 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.

• 公益社団法人 日本化学会の論文

著者

• Toda Fumio

  Department Of Applied Chemistry Faculty Of Engineering Ehime University

• Takehira Yoshikazu

  Department of Chemistry, Faculty of Engineering, Ehime University

• Takehira Yoshikazu

  Department of Industrial Chemistry, Faculty of Engineering, Ehime University

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