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Small-Ring Compounds. XXXVI. 3-Methylenecyclobutyl Bromide and 1-Methylcyclobut-2-enyl Bromide

Kiefer, Edgar F. and Roberts, John D. (1962) Small-Ring Compounds. XXXVI. 3-Methylenecyclobutyl Bromide and 1-Methylcyclobut-2-enyl Bromide. Journal of the American Chemical Society, 84 (5). pp. 784-788. ISSN 0002-7863. doi:10.1021/ja00864a021.

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3-Methylenecyclobutyl bromide and 1-methylcyclobut-2-enyl bromide have been synthesized from the cycloaddition products of allene with acrylonitrile and vinyl benzoate. The rate constants for solvolysis of the two bromides in aqueous ethanol have been determined and correlated with the solvolysis rates of a series of analogous bromides. 1-Methylcyclobut-2-enyl bromide appears to exhibit some rate enhancement due to cross-ring s-type interaction of the electrons formally centered on the 3-position with the electron-deficient 1-position in the transition state.

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Additional Information:© 1962 American Chemical Society. Received June 10, 1961. Supported by the National Science Foundation and the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is made to the Donors of the said Fund. National Science Foundation Predoctoral Fellow, 1958-1960.
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American Chemical Society Petroleum Research FundUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2706
Issue or Number:5
Record Number:CaltechAUTHORS:20151020-083704601
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Official Citation:Small-Ring Compounds. XXXVI. 3-Methylenecyclobutyl Bromide and 1-Methylcyclobut-2-enyl Bromide Edgar F. Kiefer and John D. Roberts Journal of the American Chemical Society 1962 84 (5), 784-788 DOI: 10.1021/ja00864a021
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61305
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 18:39
Last Modified:10 Nov 2021 22:47

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