Spangler, Charles W.||Graham, Laurine L.||Kevill, Dennis N.
M.S. (Master of Science)
Department of Chemistry
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.
Feldt, Robert D., "Alumina-catalyzed dehydration of isomeric octadienols" (1968). Graduate Research Theses & Dissertations. 1063.
vii, 37 pages
Northern Illinois University
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