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.
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Becker, R.S., Bost, R.O., Kolc, J., Bertionere, N.R., Smith, R.L. and Griffin, G.W. (1970) Spectroscopy and Photochemistry of Aryloxiranes. Journal of the American Chemical Society, 92, 1302-1311. https://doi.org/10.1021/ja00708a033
Trozzola, A.M., Yager, W.A., Griffin, G.W., Kristinsson, H. and Sarkar, I. (1967) Direct Evidence for the Formation of Diphenylmethylene in the Photolysis of Triphenyl- and Tetra-phenyloxirane. Journal of the American Chemical Society, 89, 3357-3358. https://doi.org/10.1021/ja00989a051
Petrellis, P.C., Dietrich, H., Meyer, E. and Griffin, G.W. (1967) Photofragmentation of Epoxides. IV. Precursors Phenylcyanocarbene. Journal of the American Chemical Society, 89, 1967-1969. https://doi.org/10.1021/ja00984a047
Griffin, G.W. (1971) Generation of Carbenes by Photochemical Cycloelimination. Angewandte Chemie International Edition in English, 10, 537-547. https://doi.org/10.1002/anie.197105371
Kristinnson, H. and Griffin, G.W. (1965) Formation of Phenylcarbenes by Photolysis of Phenyloxiranes. Angewandte Chemie International Edition in English, 4, 868. https://doi.org/10.1002/anie.196508682
White, R.C., White, K.M. and Arney Jr., B.E. (2006) Photochemistry of 1,2-Dihydronaphthalene Oxide: Concurrent Triplet and Singlet Processes via Singlet Excitation. Journal of Organic Chemistry, 71, 8173-8177. https://doi.org/10.1021/jo0614184
The Oxiranes and Carbonates (~0.05M) Were Dissolved in Acetonitrile, Placed in Quartz Tubes, Sparged with Argon, and Irradiated in a Rayonet Reactor Equipped with 8 RPR 2537 Lamps.
White, R.C. and Ma, S. (1988) Photochemistry of 4-Phenyl-1,3-Dioxolan-2-One”. Journal of Heterocyclic Chemistry, 1987, 1203 and References Found Therein; White, R.C.
Savino, T.G., Kanakarajan, K. and Platz, M.S. (1986) Unusual Temperature-Dependent Isotope Effects in the Reactions of Phenylcarbene with Cyclohexene and Cyclohexane. Journal of Organic Chemistry, 51, 1305-1309. https://doi.org/10.1021/jo00358a027
Linder, S., White, K., Palmer, M., Arney, B. and White, R.C. (2002) Geometric Requirements for the Photolysis of Aryloxiranes and Cyclic Carbonate Esters. Tetrahedron Letters, 43, 1169-1170. https://doi.org/10.1016/S0040-4039(01)02392-9
