Journal of the American Chemical Society p. 7654 - 7658 (1991)
Update date:2022-08-11
Topics:
Adam, Waldemar
Curci, Ruggero
Nu?ez, Maria Elena González
Mello, Rossella
Ketone-free solutions of methyl(trifluoromethyl)dioxirane (1) were obtained for the first time in several inert solvents, which enabled the study of the thermal and photochemical decompositions of dioxirane 1 in gas, solution, and matrix phases. Vacuum flash pyrolysis of dioxirane 1 afforded exclusively methyl trifluoroacetate (3a). Both gas- and liquid-phase photolyses and thermal liquid-phase decomposition of dioxirane 1 involve a radical chain process, initiated by attack of CH3 and CF3 radicals on dioxirane 1 to give α-alkoxy-substituted alkoxy radicals as intermediates; the latter are responsible for the production of esters 3a-d. Matrix-phase photolysis of dioxirane 1 led to methyl trifluoroacetate (3a) and 1,1,1 -trifluoroethane as main products, while gas-phase pyrolysis gave exclusively the ester 3a.
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