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Small-ring compounds—XXIX A reinvestigation of the solvolysis of cyclopropylcarbinyl chloride in aqueous ethanol. Isomerization of cyclopropylcarbinol

Caserio, Marjorie C. and Graham, William H. and Roberts, John D. (1960) Small-ring compounds—XXIX A reinvestigation of the solvolysis of cyclopropylcarbinyl chloride in aqueous ethanol. Isomerization of cyclopropylcarbinol. Tetrahedron, 11 (3). pp. 171-182. ISSN 0040-4020. http://resolver.caltech.edu/CaltechAUTHORS:20151026-142341086

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Abstract

The solvolysis of cyclopropylcarbinyl chloride in 80% ethanol is attended by substantial rearrangement—not only do the solvolysis products include cyclobutyl and allylcarbinyl alcohols and ethyl ethers but cyclopropylcarbinyl chloride undergoes partial rearrangement by “internal return” to cyclobutyl and allylcarbinyl chlorides. Nuclear magnetic resonance spectroscopy has been used to demonstrate that considerable isotope-position rearrangement takes place under quite mild conditions in the reactions of deuterium-labeled cyclopropylcarbinol and cyclobutanol with thionyl chloride. Isotope-position changes have been studied in the acid-induced isomerization of cyclopropylcarbinol.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/0040-4020(60)80068-3DOIArticle
http://www.sciencedirect.com/science/article/pii/0040402060800683PublisherArticle
Additional Information:© 1960 Pergamon Press Ltd. Receive 7 March 1960; in revised form 30 April 1960. This research was supported in part by a grant from the Petroleum Research Fund administered by the American Chemical Society. Grateful acknowledgment is hereby made to the donors of said fund. This research was also supported in part by the Office of Naval Research, to whom our appreciation is extended. Presented in part at the National Organic Chemistry Symposium of the Amer. Chem. Soc. June 15 Seattle (1959).
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
Caltech Arthur A. Noyes FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2554
Record Number:CaltechAUTHORS:20151026-142341086
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ID Code:61529
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:04
Last Modified:26 Oct 2015 22:04

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