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Studies of cyclopropylcarbinyl-allylcarbinyl free radicals


Rosen, Allan Joseph (1964) Studies of cyclopropylcarbinyl-allylcarbinyl free radicals. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/A61A-Z940.


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The di-t-butyl peroxide-initiated decarbonylations of cyclopropylacetaldehyde and dimethylcyclopropylacetaldehyde in the presence of benzyl mercaptan have been carried out and the chain-transfer constants of neopentane, n-butane, 2,3-dimethylbutane, methylcyclopropane, and isopropylcyclopropane with styrene at 79.1[degrees] have been determined in an attempt to ascertain the nature and number of the intermediates involved in interconversions of certain cyclopropylcarbinyl and allylcarbinyl derivatives in free-radical reactions. These interconversions are shown to be reversible. It is concluded that the nonclassical homoallyl radical and the classical allylcarbinyl radical are the intermediates involved in the free-radical interconversion of the cyclopropylcarbinyl and allylcarbinyl skeletons. No evidence is found for the existence of a nonclassical dimethylhomoallyl radical; the classical dimethylcyclopropylcarbinyl and ([gamma, gamma]-dimethylallyl)-carbinyl radicals are probably the only intermediates involved in the free-radical interconversion of the dimethylcyclopropylcarbinyl and ([gamma, gamma]-dimethylallyl)-carbinyl skeletons.

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-10012002-153114
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:3853
Deposited By: Imported from ETD-db
Deposited On:02 Oct 2002
Last Modified:21 Dec 2019 04:06

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