Abstract
The light-induced reaction of ozone with 1,3-butadiene in argon matrixes is described, using either red (625 nm) or UV (254 nm) irradiation. Products were observed using infrared spectroscopy and identification was aided by 18O and deuterium experiments. The experimental work was supported by extensive DFT calculations. Four products were anticipated to be formed, ethenyloxirane, 2-butenal, 3-butenal and 2,5-dihydrofuran, and all four were observed. These results suggested the intermediacy of a triplet biradical H2CCHCHCH2O formed through the initial step of the reaction of O 3P with butadiene. In addition, one unexpected product was conclusively identified, ethylketene, formed through a double hydrogen shift after formation of the initial triplet biradical. Some product variation was observed with the different wavelengths of irradiation, reflecting the spin multiplicity of the initially formed O atom.
Published Version
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