Epoxide formation by ring closure of the cinnamyloxy radical
[formula: see text] The cinnamyloxy and oxiranyl benzyl radicals were generated by photolysis of alkyl 4-nitrobenzenesulfenates. The yet unprecedented epoxide ring formation from a primary alkoxy radical was observed. Experimental evidence supports the fact that the mode of ring opening of the oxiranyl carbinyl radical system is thermodynamically driven. B3LYP/6-31G* calculations indicate that the closed form of the radical is approximately 5 kcal/mol more stable than the open one.
Amaudrut
J
Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556-5670, USA.
Wiest
O