Thesis - Open Access
Master of Science (MS)
The purpose of this research is to study the mechanism of alkyl migration in nitrogen ylids. There are several possible mechanisms by which the migration may take place. A. The alkyl group, R, may migrate intermolecularly. During the migration the R group would exist as a free carbonium ion separated from the parent molecule by solvent. B. The alkyl group remaining in the same plane during the migration. Isomers would not be expected because of the facile inversion about the nitrogen atoms. C. The alkyl group, R, may migrate both cis and trans, through a concerted mechanism. The alkyl group migrating to either side of the nitrogen. To study the mechanisms of alkyl migration, triazolidium ylids (1) were used in which the alkyl migration may or may not produce ring enlargement. If only ring enlargement occurs, then the rearrangement must take place via mechanism (B.) or (C.). If, however, a large amount of polymeric product (2) and only a small amount of the ring enlarged product are obtained, then the rearrangement must proceed through mechanism (A.). (see more in text)
Library of Congress Subject Headings
South Dakota State University
Bruxvoort, Wesley J., "The Mechanism of Alkyl Migrations in Nitrogen yeilds" (1968). Electronic Theses and Dissertations. 3420.