I. Carbonion- and Free Radical-Type Rearrangements in Homoallylic Systems. II. Nuclear Magnetic Resonance in Cyclopropanes

Citation

Howden, Merlin E. H. (1962) I. Carbonion- and Free Radical-Type Rearrangements in Homoallylic Systems. II. Nuclear Magnetic Resonance in Cyclopropanes. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/J9CT-A176. https://resolver.caltech.edu/CaltechTHESIS:08162011-081910216

Abstract

I. A study was made of the Grignard and free-radical reactions of vinyl-and phenyl-substituted allyl-carbinyl derivatives. Cyclopropylcarbinyl products were obtained in both types of reactions for the ([...]-vinylallyl)-carbinyl and ([...], [...]-diphenylallyl)-carbinyl systems, and evidence was obtained bearing on the intermediates involved in some of these rearrangements.

II. Analysis of the nuclear magnetic resonance spectra of a number of cyclopropanes yielded data in the form of spin-spin coupling constants and chemical shifts. This information was correlated with existing theories on molecular structure and on the electronic structure of cyclopropanes. The chemical shifts for several cyclopropane hydrocarbons were interpreted in part in terms of a cyclopropane ring current effect.

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