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Published August 1, 1956 | public
Journal Article

Small-Ring Compounds. XV. Methylenecyclobutene and Related Substances

Abstract

Methylenecyclobutene has been synthesized from diethyl methylenemalonate by way of 3-methylenecyclobutanecarboxylic acid and 3-rnethylenecyclobutylamine. The synthesis featured the use of anthracene as a blocking group for the exocyclic double bond during malonic-ester closure of the cyclobutane ring. 4,4-Dimethyl-3-methylenecyclobutene has been obtained by degradation of α-pinene and 1-phenyl-3-methylenecyclobutene by condensation of allene with phenylacetylene. Bromine addition and three types of polymerization of methylenecyclobutene have been found to proceed in accordance with predictions based on simple molecular-orbital theory. 3-Methylenetrimethylene oxide, of interest because of the possibility that it might have demonstrable π-bonding across the ring, has been prepared.

Additional Information

© 1956 American Chemical Society. Received January 16, 1956. Supported in part by the Petroleum Research Fund of the American Chemical Society and presented before the Meeting of the American Chemical Society at Minneapolis, September 16, 1955. National Science Foundation Predoctoral Fellow, 1953-1955.

Additional details

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