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Carbonium ion intermediates from allycarbinyl and cyclopropylcarbinyl derivatives

Citation

Kover, Warner Bruce (1964) Carbonium ion intermediates from allycarbinyl and cyclopropylcarbinyl derivatives. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-09252002-143022

Abstract

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The products of the amine-nitrous acid reaction of ([alpha]-methylallyl)-carbinylamine were determined. The deamination of dideutero-([beta]-methylallyl)-carbinylamine was found to yield apparently unrearranged dideutero-([beta]-methylallyl)-carbinol and 1-methylcyclobutanol with > 97% of the deuterium in the 3-position. The deamination of dideutero-([alpha]-methylallyl)-carbinylamine was found to yield methylallylcarbinol with 78% of the deuterium in the [alpha]-methylene position and (2-methylcyclopropyl)-carbinol with 66% of the deuterium on the cyclopropyl ring. The deamination of dideutero-(2-methylcyclopropyl)-carbinylamine was found to yield methylallylcarbinol with 74% of the deuterium in the vinyl methylene position and (2-methylcyclopropyl)-carbinol with 85% of the deuterium on the carbinyl carbon.

These results are discussed in terms of various intermediates. It is concluded that the experimental evidence appears to require interpretation in terms of the equilibrating nonclassical bicyclobutonium and homoallylic carbonium 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):
  • Unknown, Unknown
Thesis Committee:
  • Unknown, Unknown
Defense Date:1 January 1964
Record Number:CaltechETD:etd-09252002-143022
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-09252002-143022
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:3759
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:26 Sep 2002
Last Modified:26 Dec 2012 03:02

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