Rearrangements in the Solvolysis of 2-Butyl-1-C^(14) p-Toluenesulfonate
Abstract
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.
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.Additional details
- Eprint ID
- 61442
- DOI
- 10.1021/ja01137a013
- Resolver ID
- CaltechAUTHORS:20151022-140104698
- Atomic Energy Commission
- Created
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2015-10-22Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field