ipso‐Substitution with Sodium‐N‐alkyl‐(p‐nitrobenzene)sulfonamide. A novel anionic rearrangement

1979/03/07 by Paul Müller, Nguyen‐Thi Minh Phuong · 1 citation
Chemistry · #Chemical Reaction Mechanisms #Inorganic and Organometallic Chemistry #Analytical chemistry methods development

paper · doi:10.1002/hlca.19790620215

Abstract

Abstract Reaction of N ‐benzyl‐ N , N ‐di‐( p ‐nitrobenzene)sulfonamide ( 3 ) with NaCN/HMPA at 140° affords N ‐benzyl‐ p ‐nitroaniline ( 4 ). The same product is obtained upon heating of the sodium salt of N ‐benzyl‐( p ‐nitrobenzene)sulfonamide ( 5 ). The transformation 5 → 4 is believed to proceed via an anionic episulfonyl compound 6 .

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