Publication Date

1968

Document Type

Dissertation/Thesis

First Advisor

Spangler, Charles W.||Graham, Laurine L.||Kevill, Dennis N.

Degree Name

M.S. (Master of Science)

Department

Department of Chemistry

LCSH

Chemistry

Abstract

The alumina-catalyzed dehydration of isomeric octadienols, resulting in octatriene formation, was studied in detail. The octatriene system was chosen for the following reasons: (1) to determine the extent of 1,2 versus 1,6 dehydration over alumina, (2) to determine if the cyclization of intermediate trienes followed the Woodward-Hoffmann scheme, and (3) to determine if other heretofore unknown processes occur during dienol dehydration. l,3-Octadien-5-ol and 2,4-octadien-6-ol were catalytically dehydrated over alumina to give products which gave similar gas-liqu1d partition chromatograms. 2,4,6-Octatriene, 1,3,5-octatriene and l,6-d1methyl-l,3-cyclohexadiene were isolated and identified. Another product partially Identified 1s a cyclohexadiene with at least one vinyl methyl group. The extent of 1,2 versus 1,6 dehydration over alumina was found to be 2:1 for 2,4-octadien-6-ol but it was impossible to determine if the cyclization followed the Woodward-Hoffmann scheme. The results indicate that both triene-triene rearrangement and diene-diene rearrangement occur over alumina. This represents a new aspect of dienol dehydration.

Comments

Includes bibliographical references.||Includes illustrations.

Extent

vii, 37 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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