Alkylation of the ambident formanilide anion.

Tan, See-Hua (1971) Alkylation of the ambident formanilide anion. Masters thesis, Memorial University of Newfoundland.

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Abstract

Benzylation of lithium, potassium, tetraethylammonium and silver salts of the ambident formanilide anion under different reaction conditions has been studied. -- The lithium, potassium and tetraethylammonium salts generally gave exclusively N-benzylation whereas the reaction with silver salts occurred predominantly on oxygen. The choice of solvent, the halide of the benzyl halide, and the substituent on the alkylating agent and/or formanilide did not affect the site of alkylation of the alkali metal salts but the oxygen and nitrogen alkylation product distribution from the silver salt alkylations did depend, to some extent, upon these factors. The highest O-alkylation in the case of the silver salt was always obtained in dimethoxyethane, while the reaction in dimethylformamide gave comparatively high yields of N--alkylation product. Exceptional cases are reported where N-alkylation was predominate in silver salt alkylations and these will be discussed. -- A number of formiminoalkyl ethers and N-alkylformanilides were isolated and their spectra are compared.

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