Mechanism of formation of p-aminobenzyl aryl sulfides, selenides, or sulfones by the acid-catalyzed condensation of aromatic amines with formaldehyde and …

IE Pollak, GF Grillot

Index: Pollak,I.E.; Grillot,G.F. Journal of Organic Chemistry, 1967 , vol. 32, p. 3101 - 3108

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Citation Number: 11

Abstract

Evidence is brought against the significance of a resonance-stabilized carbonium-sulfonium ion that has been postulated in the literature to account for the formation of p-aminobenzyl aryl sulfides when arenethiols are condensed with formaldehyde and aromatic amines in the presence of mineral acids. A new mechanism is postulated that accounts very satisfactorily not only for the formation of these sulfides but also for the formation of the analogous ...