高等学校化学学报 ›› 1990, Vol. 11 ›› Issue (4): 371.

• 研究论文 • 上一篇    下一篇

(Z)-1,2-二苯基-1,3-丁二烯与单取代的乙烯衍生物区位选择性环加成反应

谢周, 徐贤恭   

  1. 中山大学化学系
  • 收稿日期:1988-11-15 出版日期:1990-04-24 发布日期:1990-04-24
  • 通讯作者: 谢周

Regiosclective Cycloaddition Reaction of (Z)-1 ,2-Diphcnyl-1,3-butadiene with Monosubstituted Ethylenes

Xie Zhou, Xu Xiangong   

  1. Department of Chemistry, Zhougshan University, Guangzhou
  • Received:1988-11-15 Online:1990-04-24 Published:1990-04-24

摘要: (Z)-1,2-二苯基-1,3-丁二烯分别与甲基乙烯基酮、丙烯酰胺、丙烯腈以及丙烯醛发生环加成反应,均生成顺式和反式的连位取代环己烯衍生物。以IR、1HNMR和MS鉴定了产物的结构。利用CNDO/2法计算了分子轨道能量和系数,由前线分子轨道理论解释了这种环加成反应的区位选择性。

关键词: 双烯合成, 区位选择性, 二苯基丁二烯, CNDO/2法, 前线分子轨道理论

Abstract: The cycloaddition reactions of (Z)-J ,2-diphenyl-1, 3-butadiene were studied with a high regioselectivity. The products were identified by IR, NMRand MS. The regioselectivity in the Diels-Alder reactions of (Z)-1 ,2-diphenyl-1,3-butadiene can be rationalized by frontier orbital theory. The primary orbital interactions which have been used to predict the regioselectivity in the Diels-Alder reaction could not account for the regioselectivity observed with (Z)-1,2-diphenyl-1,3-butadiene. When the secondary orbital interactions were included in the theory, the preferred regioisomer was rationalized in every case. The frontier molecular orbitals of (Z)-1, 2-diphenyl-1, 3-butadiene and the dienophiles were determined by the CNDO/2 method.

Key words: Diene synthesis, Regioselectivity, Diphenylbutadiene, CNDO/2 method, Frontier molecular orbital theory

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