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I. An investigation of rearrangement in 2-phenylethyl organometallic compounds. II. Skeletal interconversion in allylcarbinyl, cyclo-propylcarbinyl and cyclobutyl Grignard reagents

Citation

Hamilton, Carole L. (1963) I. An investigation of rearrangement in 2-phenylethyl organometallic compounds. II. Skeletal interconversion in allylcarbinyl, cyclo-propylcarbinyl and cyclobutyl Grignard reagents. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechTHESIS:03142012-092542581

Abstract

I. An investigation of rearrangement in 2-phenylethyl organometallic compounds. The Grignard reagent formed by 2-phenylethyl-l-14C chloride has been shown not to undergo significant isotope-position rearrangement. Attempts to prepare 2-phenylethyllithium are discussed.

II. Skeletal interconversion in allylcarbinyl, cyclo-propylcarbinyl and cyclobutyl Grignard reagents. The Grignard reagents have been prepared from allylcarbinyl, cyclopropylcarbinyl, and cyclobutyl chlorides in the presence of proton donors, and rearrangement of all three skeletons has been observed. It has been established that allylcarbinylmagnesium chloride exists in equilibrium with cyclopropylcarbinylmagnesium chloride, the former being very much favored. Evidence for the existence of a non-classical homoallyl free radical is presented.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Chemistry
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 1963
Record Number:CaltechTHESIS:03142012-092542581
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:03142012-092542581
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:6850
Collection:CaltechTHESIS
Deposited By: Tony Diaz
Deposited On:27 Mar 2012 18:00
Last Modified:26 Dec 2012 04:40

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