Epoxide formation by ring closure of the cinnamyloxy radical

Article abstract of DOI:10.1021/ol005749t

(equation presented) Ar = 4-nitrobenzene 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 ～5 kcal/mol more stable than the open one.