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Evidence for Cyclopentyne as a Reaction Intermediate in the Coupling of Phenyllithium with 1-Chlorocyclopentene

Roberts, John D. (1960) Evidence for Cyclopentyne as a Reaction Intermediate in the Coupling of Phenyllithium with 1-Chlorocyclopentene. Journal of the American Chemical Society, 82 (17). pp. 4750-4751. ISSN 0002-7863.

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Evidence has been presented previously for the intervention of benzyne and cyclohexyne as intermediates in nucleophilic substitution reactions of phenyl and cyclohexenyl halides, respectively. In studies designed to determine the minimum ring size for operation of the elimination-addition mechanism, we have now found that an entity with the symmetry properties of cyclopentyne must be involved in the formation of 1-phenylcyclopentene from 1-chlorocyclopentene-1-^(14)C and phenyllithium.

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Additional Information:© 1960 American Chemical Society. Received July 20, 1960. Supported in part by the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is hereby made to the Donors of this Fund.
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American Chemical Society Petroleum Research FundUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2605
Issue or Number:17
Record Number:CaltechAUTHORS:20151020-095616175
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Official Citation:EVIDENCE FOR CYCLOPENTYNE AS A REACTION INTERMEDIATE IN THE COUPLING OF PHENYLLITHIUM WITH 1-CHLOROCYCLOPENTENE John D. Roberts Journal of the American Chemical Society 1960 82 (17), 4750-4751 DOI: 10.1021/ja01502a081
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61317
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 18:12
Last Modified:03 Oct 2019 09:06

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