| 3,5-二烷氧基甲苯的溴化反应研究 |
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| 引用本文： | 顾烨,石洪卫,陈丽媛,沈永嘉. 3,5-二烷氧基甲苯的溴化反应研究[J]. 有机化学, 2012, 32(1): 174-177 |
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| 作者姓名： | 顾烨 石洪卫 陈丽媛 沈永嘉 |
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| 作者单位： | 华东理工大学精细化工研究所 结构可控先进功能材料及其制备教育部重点实验室 上海200237 |
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| 摘 要： | 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.
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| 关 键 词： | 3,5-二甲氧基甲苯 3,5-二乙酰氧基甲苯 N-溴代丁二酰亚胺 3,5-二乙酰氧基苄溴 |
Bromination of 3,5-Dialkyloxytoluene |
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| Gu,Ye , Shi,Hongwei , Chen,Liyuan , Shen,Yongjia. Bromination of 3,5-Dialkyloxytoluene[J]. Chinese Journal of Organic Chemistry, 2012, 32(1): 174-177 |
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| Authors: | Gu Ye Shi Hongwei Chen Liyuan Shen Yongjia |
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| Affiliation: | Gu,Ye Shi,Hongwei Chen,Liyuan Shen,Yongjia(Laboratory for Advanced Materials,Institute of Fine Chemicals,East China University of Science and TechnologShanghai 200237) |
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| Abstract: | When 3,5-dimethoxy-toluene reacted with N-bromosuccinimide(NBS) in the presence of azobisisobutyronitrile,the product was not 3,5-dimethoxy benzylbromide,but a mixture of 2-bromo-3,5-dimethoxy-toluene and 2,6-dibromo-3,5-dimethoxy-toluene.Under the same conditions,3,5-diacetoxy-toluene reacted with NBS to generate 3,5-diacetoxy-benzyl bro-mide.The charge density distributions calculated by GAUSSIAN 03 indicated that the charge density of carbon atom of ben-zene ring in 3,5-dimethoxy-toluene was higher than the one of the carbon atom of the side chain.Thus,bromine radical was easy to replace the hydrogen in the ring.While the charge density distributions of 3,5-diacetoxy toluene was quite the opposite,hence,the product was 3,5-diacetoxy-benzyl bromide. |
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| Keywords: | 3,5-dimethoxy-toluene 3,5-diacetoxy-toluene N-bromosuccinimide 3,5-diacetoxy-benzyl bromide |
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