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Photochemistry of Styrene Oxide: A Triplet Pathway in the Singlet Excitation of a Monoaryl Oxirane
Department of Chemistry, Sam Houston State University, Huntsville, TX, USA
University of Siegen, Siegen, Germany
Department of Chemistry, Sam Houston State University, Huntsville, TX, USA
- 1 Department of Chemistry, Sam Houston State University, Huntsville, TX, USA
- 2 University of Siegen, Siegen, Germany
- 3 Department of Chemistry, Sam Houston State University, Huntsville, TX, USA
International Journal of Organic Chemistry·Volume 07 (2017)·Pages 263–268·Published 21 July 2017·DOI10.4236/ijoc.2017.73020
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Abstract
Direct photolysis and quenching experiments with styrene oxide support the existence of an efficient triplet photochemical pathway to benzyl radical formation. Similar photolytic behavior for styrene glycol carbonate strongly supports the 1,3-diradical, resulting from the scission of the benzylic C-O bond, as the geometric source of the triplet pathway. Primary photoproducts were determined by both NMR and HPLC analysis and we observed that toluene and bibenzyl were both primary photoproducts, not secondary photoproducts.
KeywordsPhotochemistryOxiranesCyclic Carbonate EstersMechanisms
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