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Small-Ring Compounds. XLIII. Formolysis of Substituted Allylcarbinyl Tosylates

Servis, Kenneth L. and Roberts, John D. (1965) Small-Ring Compounds. XLIII. Formolysis of Substituted Allylcarbinyl Tosylates. Journal of the American Chemical Society, 87 (6). pp. 1331-1339. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151016-100322036

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Abstract

Rate accelerations have been measured as a function of methyl substitution in 3- and 4-positions and phenyl substitution at the 4-position in the formolysis of allylcarbinyl tosylate. The largest factor, 4.5 x 10^3, was observed for (γ,γ dimethylallyl)carbinyl tosylate. The nature of the solvolytic transition state is discussed; the results are shown to be inconsistent with formation of classical carbonium ion intermediates.


Item Type:Article
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http:/dx.doi.org/10.1021/ja01084a031DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01084a031PublisherArticle
Additional Information:© 1965 American Chemical Society. Received November 13, 1964. Supported in part by the National Science Foundation.
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry3170
Issue or Number:6
Record Number:CaltechAUTHORS:20151016-100322036
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151016-100322036
Official Citation:Small-Ring Compounds. XLIII. Formolysis of Substituted Allylcarbinyl Tosylates Kenneth L. Servis and John D. Roberts Journal of the American Chemical Society 1965 87 (6), 1331-1339 DOI: 10.1021/ja01084a031
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61196
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 17:13
Last Modified:03 Oct 2019 09:05

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