Date of Award
Doctor of Philosophy
The thermal rearrangement of the dimer of butadiene (32), 4-vinyl-cyclohexene (34), was investigated by flash vacuum pyrolysis (FVP). The FVP of 4-vinylcyclohexene-3,3,5,5,6,6,8,8-d(,8) (34-d(,8)) at 800(DEGREES)C gave benzene (30), which had a statistical deuterium incorporation, as a major product. From the results of the study a new mechanism for the pathway from butadiene (32) to benzene (30) is proposed;Also described is a study on dibenzocyclooctene-5,5,6,6,-d(,4) (16-d(,4)) and the isolation and characterization of the minor products produced along with anthracene (13) in the FVP of 16;The VPF of 2,9-dimethyldibenzosuberone (38) gives, as the sole product, 2,6-dimethylanthracene (25). The regiospecific transfor- mation arises from a 180(DEGREES) ring flip of the two original aromatic nuclei relative to one another. The synthetic utility of this reaction;was investigated, and it is a high yield, regiospecific route to difunctionalized anthracenes; *DOE Report IS-T-1180. This work was performed under contract No. W-7405-Eng-82 with the U.S. Department of Energy.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Jay Leslie Tunkel
Tunkel, Jay Leslie, "Formation of benzene by the pyrolysis of 4-vinylcyclohexene Regiospecific formation of anthracenes in the pyrolysis of dibenzosuberones and related systems " (1985). Retrospective Theses and Dissertations. 7892.