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

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.

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