Reaction of N-Haloamide. VIII. Reactions of N-Bromobenzenesulfonamides or Bromine with Benzylamines

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Reaction of N-bromo-N-benzylbenzenesulfonamide (2), N, N-dibromobenzenesulfonamide, and bromine with benzylamines were studied. Tertiary benzylamine degraded to secondary benzylamine hydrobromide and benzaldehyde, secondary benzylamine to primary benzylamine hydrobromide and benzaldehyde, and primary benzylamine to ammonia, benzaldehyde, and primary benzylamine hydrobromide in moist benzene. When the reaction was carried out in dried medium, several intermediates such as salts of benzalbenzylamine (8, 9) and benzalbenzenesulfonamide were identified. The structure of an intermediate, benzalbenzylamine hydrobromide perbromide (9) was established.

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