Reaction of N-Haloamide. XXII. Reaction of N, N-Dibromobenzenesulfonamide with Safrole

Abstract

N, N-Dibromobenzenesulfonamide (II) was made to react with safrole (I) to give 2-benzenesulfonamido-3-bromo-1-(3', 4'-methylenedioxyphenyl) propane (III), 2-benzenesulfonamido-3-bromo-1-(6'-bromo-3', 4'-methylenedioxyphenyl) propane (IV), 1-benzenesulfonamido-3-bromo-2-(3', 4'-methylenedioxyphenyl) propane (VI), 1-benzenesulfonamido-3-bromo-2-(6'-bromo-3', 4'-methylenedioxyphenyl) propane (VII) and a mixture of bromo-adducts of safrole (XI) as by-product. The productions of VI and VII show that a Wagner-Meerwein rearrangement occurred in the course of the addition of II to the double bond of I.