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Evidence for cyclohexyne as an intermediate in the coupling of phenyllithium with 1-chlorocyclohexene

Scardiglia, F. and Roberts, John D. (1957) Evidence for cyclohexyne as an intermediate in the coupling of phenyllithium with 1-chlorocyclohexene. Tetrahedron, 1 (4). pp. 343-344. ISSN 0040-4020. doi:10.1016/0040-4020(57)88011-9.

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Elimination-Adition mechanisms involving "benzyne"-type (C_6H_4) intermediates have been established for the rearrangements which occur in the amination of non-activated aryl halides, high temperature alkaline hydrolysis of aryl halides and the coupling of phenyllithium with aryl halides. Wittig and Harboth have reported small yields of 1-phenylcyclohexene from the coupling of phenyllithium with 1-chlorocyclohexene and it appeared possible that this reaction might well proceed by way of cyclohexyne as an intermediate. Of interest in this connection is the report by Favorsky and Boshowsky that a cyclohyexne trimer (dodecahydrotriphenylene) is formed in the reaction of 1,2-dibromocyclohexene with sodium.

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Additional Information:© 1957 Pergamon Press Ltd. Received 23 July 1957. Supported in part by the Petroleum Research Fund administered by the American Chemical Society. Grateful acknowledgement is hereby made to the Donors of the Fund. Obtained from the Radiation Laboratory of the University of California on allocation by the U.S. Atomic Energy Commission. Contribution No. 2230 from the Gates and Crellin Laboratories of Chemistry, California Institute of Technology Pasadena, California U.S.A.
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American Chemical Society Petroleum Research FundUNSPECIFIED
Atomic Energy CommissionUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry 2230
Issue or Number:4
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ID Code:61532
Deposited On:27 Oct 2015 16:11
Last Modified:10 Nov 2021 22:50

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