I. An Investigation of Rearrangement in 2-Phenylethyl Organometallic Compounds. II. Skeletal Interconversion in AIIylcarbinyl Cyclopropylcarbinyl and Cyclobutyl Grignard Reagents

Author: Hamilton, Carole Lois

Year: 1963

Degree: Dissertation (Ph.D.)

Advisor: Roberts, John D.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/D4XP-HN97

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.

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