Elsevier

Tetrahedron Letters

Volume 41, Issue 45, 4 November 2000, Pages 8781-8785
Tetrahedron Letters

First N-alkyl heterolysis of tertiary benzamides in neutral conditions

https://doi.org/10.1016/S0040-4039(00)01555-0Get rights and content

Abstract

Tertiary benzamides 14 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).

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