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Rearrangements in the Solvolysis of 2-Butyl-1-C^(14) p-Toluenesulfonate

Roberts, John D. and Bennett, Winifred and McMahon, Robert E. and Holroyd, Edmond W. (1952) Rearrangements in the Solvolysis of 2-Butyl-1-C^(14) p-Toluenesulfonate. Journal of the American Chemical Society, 74 (17). pp. 4283-4286. ISSN 0002-7863. doi:10.1021/ja01137a013.

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Solvolysis of 2-butyl-1-C^(14)p-toluenesulfonate in acetic acid in the presence of acetate ion under conditions where the reaction rate is essentially independent of the acetate ion concentration leads to a mixture of 91 ± 1% of 2-butyl-1-C^(14) acetate and 9 ± 1% of the rearranged product, 2-butyl-4-C^(14) acetate. It has been shown that the rearrangement is not due to rearrangement of the starting material or to elimination to yield butenes followed by addition of acetic acid. Much less rearrangement occurs in the hydrolysis of 2-butyl-1-1-C^(14) p-toluenesulfonate in 75% acetone-25% water (by volume). It is concluded that a non-classical cation of the type CH_3CH-CHCH_2 is not an important intermediate in the unimolecular hydrolysis or acetolysis of 2-butyl p-toluenesulfonate.

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Additional Information:© 1952 American Chemical Society. Received February 8, 1952. Supported in part by the joint program of the Office of Naval Research and the United States Atomic Energy Commission. Presented in part at the Symposium on Reaction Mechanisms at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951. We are pleased to acknowledge the aid of Dr. G. R. Coraor and Mrs. Clare M. Regan with some of the experimental work.
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Atomic Energy CommissionUNSPECIFIED
Issue or Number:17
Record Number:CaltechAUTHORS:20151022-140104698
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Official Citation:Rearrangements in the Solvolysis of 2-Butyl-1-C14 p-Toluenesulfonate John D. Roberts, Winifred Bennett, Robert E. McMahon, and Edmond W. Holroyd Jr. Journal of the American Chemical Society 1952 74 (17), 4283-4286 DOI: 10.1021/ja01137a013
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61442
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 22:10
Last Modified:10 Nov 2021 22:49

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