I. Exploration of a synthetic route to endo-5-trimethylsilyl norborn-2-ene; II. Solvent effects in the tri-n-butyl tin hydride reduction of alkyl bromides; III. Hydroboration of (chloroethynyl)trimethylsilane

Author

John C. Camp

Publication Date

1974

Document Type

Dissertation/Thesis

First Advisor

Cunico, Robert F.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry

LCSH

Organic chemistry

Abstract

A project to unequivocally characterize both endo- and exo-5-trimethylsilylnorborn-2-ene was undertaken. A key intermediate in the proposed reaction sequence, endo-5-(dichlorosiloxy)norborn-2-ene, was prepared and characterized. The next step, an intramolecular hydro-silylation, proved to be impossible to effect under all reaction conditions tried, polymerization occurring instead. The spectral assignments of these endo- and exo-5-trimethylsilylnorborn-2-enes are therefore still in doubt. The reduction of alkyl halides with tin hydrides is known to be a free radical process. Inasmuch as free radical chlorination has been shown to be markedly affected by the solvent employed, this free radical reduction was investigated to see if selective reduction could be accomplished by varying the solvent in which it is carried out. There was no significant solvent effect noted in this series of reactions. As a reactant in other projects, synthetically useful quantities of cis-chlorovinyltrimethylsilane were desired. As preparations in the literature afford this in very minor amounts, another preparation sequence was attempted. This method involved preparation of (chloro-ethynyl)trimethylsilane followed by its reduction via hydroboration, a sequence known to produce cis-alkenes in high yields in all-carbon analogues. In the present system, however, dihydroboration resulted, yielding a mixture of products which contained insignificant amounts of the desired olefin.

Comments

Includes bibliographical references.||Includes illustrations.

Recommended Citation

Camp, John C., "I. Exploration of a synthetic route to endo-5-trimethylsilyl norborn-2-ene; II. Solvent effects in the tri-n-butyl tin hydride reduction of alkyl bromides; III. Hydroboration of (chloroethynyl)trimethylsilane" (1974). Graduate Research Theses & Dissertations. 3437.
https://huskiecommons.lib.niu.edu/allgraduate-thesesdissertations/3437

Extent

v, 55 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

Text