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

Citation

Hamilton, Carole Lois (1963) I. An Investigation of Rearrangement in 2-Phenylethyl Organometallic Compounds. II. Skeletal Interconversion in AIIylcarbinyl Cyclopropylcarbinyl and Cyclobutyl Grignard Reagents. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/D4XP-HN97. https://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.

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