Spin-trapping with 2-methyl-2-nitrosopropane: photochemistry of carbonyl-containing compounds. Methyl radical formation from dimethyl sulfoxide

Article abstract of DOI:10.1139/v82-215

The photochemical reactions of several carbonyl-containing compounds investigated by spin-trapping with 2-methyl-2-nitrosopropane revealed different modes of scission depending on the structure of the initial compound.Thus, in photo-Fries rearrangements, the acyl radical was detected. 1,3-diphenyl-2-propanone decarbonylated to yield the benzyl radical.Finally, valerophenone yielded the radicals expected by γ-hydrogen abstraction.In a dark reaction, dimethyl sulfoxide reacts with NaOH to generate methyl radicals.The latter result suggests the need for caution in the use of dimethyl sulfoxide with 2-methyl-2-nitrosopropane for the detection of hydroxyl radicals.