First N-alkyl heterolysis of tertiary benzamides in neutral conditions

Tertiary benzamides 1–4 bearing a tricyclopropylmethyl substituent were synthesized and found to undergo rapid alkyl-nitrogen heterolysis at pH 7. X-Ray diffraction structural data for these amides revealed that their ability to give N-alkyl fission was not induced by the pyramidalization of the nitrogen atom, in contrast to what has been observed in the case of N-acyl cleavage (hydrolysis).