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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. http://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.

Item Type:Thesis (Dissertation (Ph.D.))
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Roberts, John D.
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1959
Record Number:CaltechETD:etd-02172006-092624
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-02172006-092624
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:656
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:21 Feb 2006
Last Modified:26 Dec 2012 02:31

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