Intermediates in Carbonium Ion Reactions of Methyl-Substituted Cyclopropylcarbinyl Cyclobutyl and Allylcarbinyl Derivatives

Citation

Silver, Marc Stamm (1959) Intermediates in Carbonium Ion Reactions of Methyl-Substituted Cyclopropylcarbinyl Cyclobutyl and Allylcarbinyl Derivatives. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/PZ7V-9K90. https://resolver.caltech.edu/CaltechETD:etd-02172006-092624

Abstract

The products of the nitrous acidination of 2-methylcyclobutylamine, 3-methylcyclobutylamine, 2-methylcyclopropylcarbinylamine, cyclopropylmethylcarbinylamine, allylmethylcarbinylamine and crotylcarbinylamine have been determined. In addition, studies on the rates of solvolysis of suitable derivatives of the same carbon skeleton have been carried out. The experimental data are reminiscent of those reported for the reactions of unsubstituted cyclobutyl, cyclopropylcarbinyl and allylcarbinyl compounds and are interpreted in terms of cationic intermediates closely related to those proposed for the latter substances. In the present case, the intermediates are most reasonably represented as three non-classical, unsymmetrical, non-equivalent pyramidal ions, "bicyclobutonium" ions.

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