TITLE:
Photochemistry of Styrene Oxide: A Triplet Pathway in the Singlet Excitation of a Monoaryl Oxirane
AUTHORS:
Benny E. Aney, Heiko Ihmels, Rick C. White
KEYWORDS:
Photochemistry, Oxiranes, Cyclic Carbonate Esters, Mechanisms
JOURNAL NAME:
International Journal of Organic Chemistry,
Vol.7 No.3,
September
1,
2017
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.