Neophyl halides

Displacements. Primary and secondary alkyl chlorides react rapidly and exother-mally with sodium cyanide in partial solution in dimethyl sulfoxide to give the corresponding nitriles in excellent yield. - The reactions are faster and the yields better than in the reactions of the corresponding bromides or iodides in aqueous alcohol. Neopentyl and neophyl halides can be converted by this method to... 

CsH5C(CHs)>CH>1. Neophyl iodide, prepared (59) from neophyl chloride (58) reacted with K3Co(CN).-> in the same way, except that 12 ml. of benzene were added to disperse the halide, and reaction time was 20 hours. The infrared spectrum of the light brown solid product isolated exhibited CN stretch bands at 2125 and 2089 cm." Acidification followed by alkali treatment yielded neophyl cyanide (infrared and PMR analysis). 

Neopentyl and Neophyl Iodides. The halides mentioned above formed the corresponding organocobalt complexes on reaction with pentacyanocobaltate(II). While neopentyl radical is stable to rearrangement, the neophyl radical undergoes aryl migration (56) as follows ... 

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