Published August 1, 1958 | public
Journal Article

Small-Ring Compounds. XVIII. Alkali-induced Ring Opening of Some Phenylcyclobutenone Derivatives

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Abstract

Phenylcyclobutenedione (I) has been found to decompose by the action of alkali to benzylidenepyruvic acid (X) and benzaldehyde. Similarly 2-hydroxy-3-phenyl-2-cyclobutenone (V) yields benzylpyruvic acid (VII), and 4-hydroxy-3-phenylcyclobutenedione (XI) gives phenylpyruvic acid (XII) and 1,3-diphenylpropene (XIII). Possible reaction mechanisms for the formation of these substances are proposed.

Additional Information

© 1958 American Chemical Society. Received January 9, 1958. Supported in part by the National Science Foundation.

Additional details

Created:
August 19, 2023
Modified:
October 25, 2023