Spangler, Charles W.
M.S. (Master of Science)
Department of Chemistry
[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.
Ahmad, Salmiah, "Thermolytic studies of 5-alkyl and 5-vinyl substituted 1, 3-cyclohexadienes" (1980). Graduate Research Theses & Dissertations. 6441.
Northern Illinois University
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