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3,5-二甲氧基甲苯在偶氮二异丁腈的存在下与N-溴代丁二酰亚胺(NBS)反应,产物不是3,5-二甲氧基苄溴,而是2-溴-3,5-二甲氧基甲苯和2,6-二溴-3,5-二甲氧基甲苯.同样条件下,3,5-二乙酰氧基甲苯与NBS反应则生成3,5-二乙酰氧基苄溴.GAUSSIAN 03计算的结果表明,3,5-二甲氧基甲苯中苯环碳原子上的电荷密度高于侧链上碳原子上的电荷密度,因此溴自由基更容易取代苯环上的氢,而3,5-二乙酰氧基甲苯的情况恰好相反,故产物是3,5-二乙酰氧基苄溴.
3,5-Dimethoxytoluene is reacted with N-bromosuccinimide (NBS) in the presence of azobisisobutyronitrile instead of 3,5-dimethoxybenzyl bromide, but instead of 2 3,5-dimethoxytoluene and 2,6-dibromo-3,5-dimethoxytoluene.Under the same conditions, 3,5-diacetoxytoluene reacted with NBS to give 3, 5-diacetoxybenzyl bromide.GAUSSIAN 03 The calculated results show that the charge density on the benzene ring carbon atoms in 3,5-dimethoxytoluene is higher than the charge density on the carbon atoms in the side chain, and therefore the bromine radical More easily substituted benzene ring hydrogen, and 3,5-diacetoxytoluene the case is the opposite, so the product is 3,5-diacetoxybenzyl bromide.