高等学校化学学报

高等学校化学学报 ›› 1991, Vol. 12 ›› Issue (7): 897.

• 论文 • 上一篇    下一篇

噻吩基1,2-迁移制备2-噻吩基酸类的研究

王建华, 张西国   

  1. 西北大学化学系, 西安, 710069
  • 收稿日期:1989-10-21 出版日期:1991-07-24 发布日期:1991-07-24
  • 通讯作者: 王建华

Preparation of 2-Thienyl Carboxylic Acids via 1,2-Thienyl Migration

Wang Jian-hua, Zhang Xi-guo   

  1. Department of Chemistry, Northwest University, Xian, 710069
  • Received:1989-10-21 Online:1991-07-24 Published:1991-07-24

PDF (PC)

被引次数

3

摘要： 以α-卤代烷基噻吩基酮为原料,制得2-(2-噻吩基)丙酸、2-(5-溴-2-噻吩基)丙酸和2-(5-乙基-2-噻吩基)丙酸,研完了α-卤代烷基噻吩基酮的迁移基团、烷基、离去基、催化剂、温度和溶剂等对重排的影响,以及光学活性的2-(5-乙基-2-噻吩基)丙酸的制备,证明噻吩基1,2-迁移属邻基参与的SN2缺电子重排。

关键词: 1, 2-迁移重排, 噻吩酸, 不对称合成

Abstract: 2-(2-Thienyl)propionic acid, 2-(5-bromo-2-thienyl) propionic acid and 2-(5-ethyl-2-thienyl)propionic acid were prepared from α-haloa]kyl thienyl ketones. The effects of the shift groups, alkyl substituents, leaving groups of the ketones, catalysts, temperature and solvents etc. on the rearrangement were studied. An optical active 2-(5-ethyl-2-thienyl)propionic acid was obtained in a high yield. It may be concluded that the 1,2-thienyl migration belongs to the electronic-lacking rearrangement with SN2 mechanism.

Key words: 1,2-migration rearrangement, Thienyl carboxylic acids, Asymmetric synthesis

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