Abstract
Mechanisms for the conversion of acetophenone (or benzaldehyde) to 1-phenylpropane-1,2-semidione (or phenylglyoxal radical anions) by electrolytic reduction in dimethylformamide are considered. The intermediate C 6H 5C(O −)(CH 3)CH(O −)X with X = (CH 3) 2N is implicated. The free α-hydroxy aldehyde is apparently not a precursor of the semidione. Other examples of this rearrangement with X = alkoxy groups are suggested. 2,2,4,4-Tetramethylcyclobutanone ketyl at −50° rapidly decomposes to yield 3,3,5,5-tetramethylcyclopentane-1,2-semidione in tetrahydrofuran solution. This novel carbonylation reaction is presumed to involve carbon monoxide reacting with the ketyl, or K +[CO] − reacting with the ketone. Decomposition of ketyls to yield semidiones in tetrahydrofuran solution apparently occurs only in the case of highly strained ketones.
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