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Luche, J. Chem. SOC., Cbem. Commun., 183 (1976). (7) The formation of alkane by dimerization of the alkyl groups attached to the copper was not reported in ref 4-6. Crabbe and c o -~o r k e r s~,~ used dimethyl-and diethyicuprate, in which case ethane and butane could have easily escaped detection. Landor and co-workers4 used di-n-buylcuprate in several reactions but did not report the formation of octane. (8) W H.A synthetically useful one-step procedure for converting a-arylated tertiary n i t r o compounds i n t o highly branched /3-arylated nitroparaffins is described. These reactions appear t o proceed via a chain mechanism in which radical anions a n d free radicals are intermediates.

Rearrangements occur when /3-arylated nitroparaffins react with the sodium salt of methanethiol, a finding which provides support for the view that these reactions involve a spiro free radical intermediate.1 By invoking spiro free radicals one can explain the striking solvent and substituent effects observed in the reactions of nitroparaffins with the sodium salt of methanethiol. A minor side reaction-fragmentation of radical anions derived from /3-arylated nitroparaffins-is described.

Aroylcyanide (I) reagieren mit Triphenylphosphin in Tetrachlorkohlenstoff über die Ylid‐Stufe (II) zu den 2‐Aryl‐3,3‐dichlor‐acrylnitrilen (III).