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Small-Ring Compounds. XV. Methylenecyclobutene and Related Substances

Applequist, Douglas E. and Roberts, John D. (1956) Small-Ring Compounds. XV. Methylenecyclobutene and Related Substances. Journal of the American Chemical Society, 78 (16). pp. 4012-4022. ISSN 0002-7863. doi:10.1021/ja01597a040.

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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.

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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.
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American Chemical Society Petroleum Research FundUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2072
Issue or Number:16
Record Number:CaltechAUTHORS:20151021-100829401
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Official Citation:Small-Ring Compounds. XV. Methylenecyclobutene and Related Substances Douglas E. Applequist and John D. Roberts Journal of the American Chemical Society 1956 78 (16), 4012-4022 DOI: 10.1021/ja01597a040
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61370
Deposited By: Ruth Sustaita
Deposited On:21 Oct 2015 18:49
Last Modified:10 Nov 2021 22:48

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