Reaction of Propenylbenzene Derivatives and Their Analogs. I. Reaction of N, N-Dibromobenzenesulfonamide with Propenylbenzene Derivatives

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N, N-Dibromobenzenesulfonamide (II) was reacted with propenylbenzene (Ib), p-methoxypropenylbenzene (Ic), m-methoxypropenylbenzene (Id), 3, 4-dimethoxypropenylbenzene (Ie), and 4-benzyloxy-3-methoxypropenylbenzene (If), in various molar ratios in dichloromethane. 1-Benzenesulfonamido-2-bromo-1-phenylpropane (IIIb), 1-benzenesulfonamido-2-bromo-1-(4'-methoxyphenyl) propane (IIIc), 3'-bromo-substituted analog of IIIc (IVc), 1-benzenesulfonamido-2-bromo-1-(3'-methoxyphenyl) propane (IIId), 6'-bromo-substituted analog of IIId (IVd), 1-benzenesulfonamido-2-bromo-1-(3', 4'-dimethoxyphenyl) propane (IIIe), 6'-bromo-substituted analog of IIIe (IVe), N-benzenesulfonyl-3, 4-dimethoxyaniline (V'e), 6-bromo-substituted analog of V'e (Ve), 1-benzenesulfonamido-2-bromo-1-(4'-benzyloxy-6'-bromo-3'-methoxyphenyl) propane (IVf), and N-benzenesulfonyl-6-bromo-4-benzyloxy-3-methoxyaniline (Vf) were produced as main products, respectively. Formation of the side-chain eliminated compounds (such as V'e, Ve, and Vf) has been found when reacted in a ratio of I : II of less than 1 : 1, starting from 3, 4-dialkoxypropenylbenzene, and the sulfonamido group substituted in the position from which the side chain was eliminated.