CaltechAUTHORS
  A Caltech Library Service

Small-Ring Compounds. XXXV. Studies of Rearrangements in the Nitrous Acid Deaminations of Methyl-substituted Cyclobutyl-, Cyclopropylcarbinyl- and Allylcarbinylamines

Silver, Marc S. and Caserio, Marjorie C. and Rice, Howard E. and Roberts, John D. (1961) Small-Ring Compounds. XXXV. Studies of Rearrangements in the Nitrous Acid Deaminations of Methyl-substituted Cyclobutyl-, Cyclopropylcarbinyl- and Allylcarbinylamines. Journal of the American Chemical Society, 83 (17). pp. 3671-3678. ISSN 0002-7863. doi:10.1021/ja01478a028. https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706149

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:20151020-083706149

Abstract

The compositions of the alcohol mixtures formed in nitrous acid deaminations of cyclopropylmethylcarbinylamine, (2-methylcyclopropyl)-carbinylamine, 2-methylcyclobutylamine, 3-methylcyclobutylamine, crotylcarbinylamine and allylmethylcarbinylamine have been determined. These results and the behavior of the corresponding alcohols under isomerization conditions in strongly acidic media may be explained by assuming formation of three non-equivalent, unsymmetrical, non-classical cationic intermediates analogous to those previously proposed for the carbonium ion reactions of other small ring derivatives.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01478a028DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01478a028PublisherArticle
Additional Information:© 1961 American Chemical Society. Received March 3, 1961. Supported in part by the National Science Foundation and the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is hereby made to the Donors of this Fund. Presented at the Sixteenth National Organic Chemistry Symposium of the American Chemical Society, June 15, 1959, Seattle, Wash.; of the Symposium Abstracts, p. 1-10. National Science Foundation Predoctoral Fellow, 1955-1958.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
American Chemical Society Petroleum Research FundUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry 2666
Issue or Number:17
DOI:10.1021/ja01478a028
Record Number:CaltechAUTHORS:20151020-083706149
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706149
Official Citation:Small-Ring Compounds. XXXV. Studies of Rearrangements in the Nitrous Acid Deaminations of Methyl-substituted Cyclobutyl-, Cyclopropylcarbinyl- and Allylcarbinylamines Marc S. Silver, Marjorie C. Caserio, Howard E. Rice, and John D. Roberts Journal of the American Chemical Society 1961 83 (17), 3671-3678 DOI: 10.1021/ja01478a028
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61307
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 17:15
Last Modified:10 Nov 2021 22:47

Repository Staff Only: item control page