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Small-Ring Compounds. XLI. The Formolysis of Allylcarbinyl Tosylate

Servis, Kenneth L. and Roberts, John D. (1964) Small-Ring Compounds. XLI. The Formolysis of Allylcarbinyl Tosylate. Journal of the American Chemical Society, 86 (18). pp. 3773-3777. ISSN 0002-7863. doi:10.1021/ja01072a033.

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Allylcarbinyl tosylate was found to solvolyze in 98% formic acid 3.7 times faster than n-butyl tosylate. Changes in the rate ratio with nucleophilicity of the solvent suggests different mechanisms for these solvolyses. The formolysis products of allylcarbinyl tosylate were found to be virtually identical with those from cyclobutyl tosylate. Deuterium-labeling experiments indicated complete scrambling of the methylene groups in the ring-closed products. The results are interpreted in terms of formation of bicyclobutonium ion intermediates.

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Additional Information:© 1964 American Chemical Society. Received February 12, 1964. Supported in part by National Science Foundation and the Office of Naval Research.
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Office of Naval Research (ONR)UNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3037
Issue or Number:18
Record Number:CaltechAUTHORS:20151016-112436191
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Official Citation:Small-Ring Compounds. XLI. The Formolysis of Allylcarbinyl Tosylate Kenneth L. Servis and John D. Roberts Journal of the American Chemical Society 1964 86 (18), 3773-3777 DOI: 10.1021/ja01072a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61201
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 21:39
Last Modified:10 Nov 2021 22:45

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