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Small-ring compounds—XXXVIII: Calculations of the relative stabilities of intermediates in the interconversion reactions of cyclopropylcarbinyl, cyclobutyl, and allylcarbinyl derivatives by the LCAO method

Howden, M. E. H. and Roberts, John D. (1963) Small-ring compounds—XXXVIII: Calculations of the relative stabilities of intermediates in the interconversion reactions of cyclopropylcarbinyl, cyclobutyl, and allylcarbinyl derivatives by the LCAO method. Tetrahedron, 19 (S 2). pp. 403-414. ISSN 0040-4020. doi:10.1016/S0040-4020(63)80029-0. https://resolver.caltech.edu/CaltechAUTHORS:20151026-142340213

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Abstract

The simple LCAO method with corrections for angle strain indicates that bicyclobutonium cations are likely to be more stable than homoallylic cations. The reverse is predicted to be true for the corresponding free-radical and anionic derivatives. The results are in accord with experiment.


Item Type:Article
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http://dx.doi.org/10.1016/S0040-4020(63)80029-0DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040402063800290PublisherArticle
Additional Information:© 1963 Pergamon Press Ltd. Received 3 January 1962. Supported in part by the National Science Foundation; Contribution No. 2788 from the Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California.
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Caltech Gates and Crellin Laboratories of Chemistry2788
Issue or Number:S 2
DOI:10.1016/S0040-4020(63)80029-0
Record Number:CaltechAUTHORS:20151026-142340213
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151026-142340213
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61526
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:23
Last Modified:10 Nov 2021 22:50

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