Ring-chain tautomerism of imine-amine or ketone-carbinol systems obtained by condensation of dilithio-N-substituted carboxamides or sulfonamides with benzonitrile. …

H Watanabe, CL Mao, IT Barnish…

Index: Watanabe,H. et al. Journal of Organic Chemistry, 1969 , vol. 34, # 4 p. 919 - 926

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Citation Number: 47

Abstract

Condensations of benzonitrile at the ortho position of N-substituted benzamides and N- substituted benzenesulfonamides were effected by means of n-butyllithium to form imine- amine, ring-chain tautomeric systems; in three of the four cases studied, the equilibrium was far on the side of the cyclic primary amines. All four of the primary amines were condensed with benzaldehyde to give corresponding benzal derivatives; also, the imine-amine ...