Salmiah Ahmad

Publication Date

1980

Document Type

Dissertation/Thesis

First Advisor

Spangler, Charles W.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry

LCSH

Cyclohexadienes; Thermochemistry

Abstract

[1,5] Sigmatropic migrations of hydrogen, deuterium and carbon 3 2 (SP , SP and SP hybridized) in cyclopentadiene, indene and cyclohexadiene systems, and syntheses of 5—substituted-1,3-cyclohexadienes and 5,5-disubstituted-l,3-cyclohexadienes were reviewed. 5-Ethyl-5-methylcyclohexa-l,3-diene was synthesized by base condensation of 2-methylbutanal and methyl vinyl ketone followed by reduction and dehydration. Pentane solutions of 5-ethyl-5-methylcyclohexa- 1 ,3-diene were thermolyzed under both static and flow conditions from 200°-500°C. Analysis of the thermolysis products showed that the dominant thermal process was a radical aromatization. Thus, thermolysis of 5-ethyl-5-methylcyclohexa-l,3-diene produced mainly ethylbenzene and toluene, which may be rationalized from the fact that ethyl radical is thermally more stable and more easily formed than methyl radical. No evidence for [1,5] sigmatropic migration or electrocyclic ring-opening was found.

Comments

Includes bibliographical references.

Extent

80 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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