CaltechAUTHORS
  A Caltech Library Service

Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives

Mazur, Robert H. and White, William N. and Semenow, Dorothy A. and Lee, C. C. and Silver, Marc S. and Roberts, John D. (1959) Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives. Journal of the American Chemical Society, 81 (16). pp. 4390-4398. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151020-095615050

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20151020-095615050

Abstract

Investigation of the extent of isotope-position rearrangement in carbonium ion-type reactions of ^(14)C-labeled cyclopropylcarbinyl derivatives has revealed that the three methylene groups of the starting material achieve a striking degree of equivalence between reactants and products. These results, taken in conjunction with the abnormally large solvolytic reactivities of cyclopropylcarbinyl and cyclobutyl halides and sulfonate esters, can best be accounted for by assuming rapid but not instantaneous equilibration of three isomeric non-classical unsymmetrical “bicyclobutonium” ion intermediates.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01525a073DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01525a073PublisherArticle
Additional Information:© 1959 American Chemical Society. Received September 4, 1958. Supported in part by the Petroleum Research Fund of the American Chemical Society and the U. S. Atomic Energy Commission. Grateful acknowledgment is hereby made to the Donors of the Petroleum Research Fund. Presented in part at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951; National Research Council Postdoctoral Fellow, 1953-1954; National Science Foundation Predoctoral Fellow, 1955-1958.
Funders:
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Atomic Energy CommissionUNSPECIFIED
National Research Council Postdoctoral FellowshipUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2369
Issue or Number:16
Record Number:CaltechAUTHORS:20151020-095615050
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151020-095615050
Official Citation:Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives Robert H. Mazur, William N. White, Dorothy A. Semenow, C. C. Lee, Marc S. Silver, and John D. Roberts Journal of the American Chemical Society 1959 81 (16), 4390-4398 DOI: 10.1021/ja01525a073
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61316
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 18:23
Last Modified:03 Oct 2019 09:06

Repository Staff Only: item control page