Generation and Reactions of Carbanions from Dialkylamino (Methylthio) Acetonitriles

Dialkylamino (methylthio) acetonitriles 1 have been prepared by two independent pathways. The carbanions generated from 1 in various base/solvent systems reacted with alkyl halides or electrophilic alkenes to give unstable products 2 and 5 respectively. These products were transformed into amides 3 or acids 4 and 6. On the other hand, carbanions from 1 with ethyl maleinate or ω-nitrostyrene afforded products of aliphatic vicarious nucleophilic substitution 7 while with 1-nitronaphthalene, the product of aromatic vicarious nucleophilic substitution 8.

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