270595-66-9Relevant academic research and scientific papers
Epoxide formation by ring closure of the cinnamyloxy radical
Amaudrut, Jerome,Wiest, Olaf
, p. 1251 - 1254 (2007/10/03)
(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.
