Publication Date

1976

Document Type

Dissertation/Thesis

First Advisor

Cunico, Robert F.

Degree Name

M.S. (Master of Science)

Department

Department of Chemistry

LCSH

Organolithium compounds

Abstract

This investigation was concerned with the synthesis of stereochemically pure cis- and trans-β-trimethylsilylvinyllithium. Although synthesis of the cis isomer was never realized, the trans isomer was prepared in 99+% isomeric purity, as adjudged by derivatization. Various preparations of trans-β-trimethylsilylvinyllithium are described. The low temperature reaction of cis-(β-chlorovinyl)trimethylsilane with lithium metal produced cis-trans organolithium mixtures in low yield. Room temperature transmetalation of trans-(β-trimethy1- silylvinyl)tri-n-butyltin with n-butyllithium afforded pure trans-β-trimethylsilylvinyllithium in moderate yields (53% of chlorotrimethylsilane derivatized product), while at low temperature, pure trans-β-trimethylsilylvinyllithium was formed in high yield (81-90%) as evidenced by derivatization with 1,2-dibromoethane, carbon dioxide, chlorotrimethylsilane, and n-butyl bromide. Nearly as high yields were realized from the transmetalation of trans-(β-trimethylsilylvinyl)triphenyltin with phenyllithium, but here an equilibrium situation seemed to be encountered. Attempted syntheses of a cis-stannane precursor to transmetalation are also described.

Comments

Includes bibliographical references (pages [36]-40)

Extent

60 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

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