A Caltech Library Service

Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-^(14)C (3-Butenyl-1-^(14)C-amine) with Nitrous Acid

Renk, E. and Roberts, John D. (1961) Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-^(14)C (3-Butenyl-1-^(14)C-amine) with Nitrous Acid. Journal of the American Chemical Society, 83 (4). pp. 878-881. ISSN 0002-7863. doi:10.1021/ja01465a033.

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

Use this Persistent URL to link to this item:


The isotopic analysis OF the cyclopropylcarbinol and cyclobutanol formed in the reaction of allycarbinylamine-α-^(14)C with nitrous acid has indicated that all of the possible methylene-labeled, isotope-position isomers are formed but not quite to the extent expected for statistical equilibrium. The compositions of the alcohols resulting from treatment of cyclopropylcarbinyl-,cyclobutyl- and allylcarbinylamines with nitrous acid have been measured accurately and correlated with the degree of isotope-position rearrangement obtained with ^(14)C-labeled amines. The results are in agreement with the previously postulated interpretation of these reactions as involving rapid but not instantaneous equilibration of unsymmetrical non-classical cations.

Item Type:Article
Related URLs:
URLURL TypeDescription
Additional Information:© 1961 American Chemical Society. Received September 27, 1960. Supported in part by a grant from 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, Seattle, Wash., June, 1959.
Funding AgencyGrant Number
American Chemical Society Petroleum Research FundUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry2628
Issue or Number:4
Record Number:CaltechAUTHORS:20151020-083706833
Persistent URL:
Official Citation:Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-14C (3-Butenyl-1-14C-amine) with Nitrous Acid E. Renk and John D. Roberts Journal of the American Chemical Society 1961 83 (4), 878-881 DOI: 10.1021/ja01465a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61308
Deposited By: Ruth Sustaita
Deposited On:20 Oct 2015 17:17
Last Modified:10 Nov 2021 22:47

Repository Staff Only: item control page