Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-^(14)C (3-Butenyl-1-^(14)C-amine) with Nitrous Acid
- Creators
- Renk, E.
- Roberts, John D.
Abstract
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.
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.Additional details
- Eprint ID
- 61308
- Resolver ID
- CaltechAUTHORS:20151020-083706833
- American Chemical Society Petroleum Research Fund
- Created
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2015-10-20Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 2628