Photosensitized Cis-Trans Isomerization of 2, 3-Diphenylbutene-2. Investigation of Anomalous Sensitizers for Substituted Stilbene Isomerizations

Citation

Coyne, Lelia Mary (1967) Photosensitized Cis-Trans Isomerization of 2, 3-Diphenylbutene-2. Investigation of Anomalous Sensitizers for Substituted Stilbene Isomerizations. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/8kds-1d07. https://resolver.caltech.edu/CaltechTHESIS:10122015-145521569

Abstract

The behavior of the photosensitized cis-trans isomerization of 2,3-diphenylbutene-2 was studied as a function of sensitizer energy by previously established methods. In addition, certain sensitizers for which parameters other than energy transfer are operative in inducting isomerizations, were studied in more detail. Sensitization of various stilbenes and substituted stilbenes by triphenylene is discussed in terms of excited state complex formation with stilbene. Sensitization by quinones, halogen-containing aromatics and 1,2-diketones is discussed in terms of attack by photolytically produced free radicals, either by addition to and elimination from the double bond, or in the cases of 1,2-diphenylpropene and 2,3-diphenylbutene-2, by hydrogen abstraction from one of the methyl groups and reversible abstraction by the allylic radical to produce cis-trans isomerized substrate and the structurally isomerized products, 2,3-diphenylpropene and 2,3-diphenylbutene-1.

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