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Small-Ring Compounds. XII. The Bromine Addition Products of Methylenecyclobutane

Applequist, Douglas E. and Roberts, John D. (1956) Small-Ring Compounds. XII. The Bromine Addition Products of Methylenecyclobutane. Journal of the American Chemical Society, 78 (4). pp. 874-875. ISSN 0002-7863. doi:10.1021/ja01585a046.

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The dibromide(s) (I) from addition of bromine to methylenecyclobutane has been studied by several worker but the structural evidence is confusing and inconclusive. Compound I has been reported to be reconverted to methylenecyclobutane by treatment with zinc and hydrolyzed to cyclopentanone in the presence of lead dioxide. It reacts with potassium cyanide in aqueous ethanol to give an unidentified dinitrile and with dimethylamine or trimethylamine to give both saturated (permanganate) and unsaturated products in which both bromines are displaced.

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Additional Information:© 1956 American Chemical Society. Received August 22, 1955. Supported in part by the Petroleum Research Fund of the American Chemical Society. 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 Chemistry2026
Issue or Number:4
Record Number:CaltechAUTHORS:20151021-125952929
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Official Citation:Small-Ring Compounds. XII. The Bromine Addition Products of Methylenecyclobutane Douglas E. Applequist and John D. Roberts Journal of the American Chemical Society 1956 78 (4), 874-875 DOI: 10.1021/ja01585a046
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61382
Deposited By: Ruth Sustaita
Deposited On:21 Oct 2015 22:46
Last Modified:10 Nov 2021 22:48

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