贫电子环丙烷衍生物与2-巯基苯骈噻唑的反应研究

Study on the Reaction of Electron-deficient Cyclopropane Derivatives with 2-Mercaptobenzothiazole

贫电子环丙烷衍生物1以精制四氢呋喃为溶剂,与2-巯基苯骈噻唑(2)封管加热反应,得到产物3和4.产物3经IR,MS,1HNMR,13CNMR和元素分析等数据确定其结构为:(R)-β-取代-(R)-γ-(2-巯基)苯骈噻唑基-γ-对位取代苯基丁酸或(S)-β-取代-(S)-γ-(2-巯基)苯骈噻唑基-γ-对位取代苯基丁酸(3);产物4通过IR,MS,1HNMR,13CNMR,2D-NOESY谱和元素分析等数据确定其结构为:反式-β-取代-γ-对位取代苯基-3-丁烯酸(4).对生成产物的机理也进行了推测.

Electron-deficient cyclopropane derivatives 1 in anhydrous THF reacted with 2-mercaptobenzothiazole (2) in a sealed tube to give the products 3 and 4 with high yield and stereoselectivity. The structures of 3 and 4 were identified as (R)-beta-substituted-(R)-gamma-(2-mercaptobenzothiazolyl)-gamma-p-substitutedphenylbutyric acid or (S)-beta-substituted-(S)-gamma-(2-mercaptobenzothiazolyl)-gamma-p-substituted-phenylbutyric acid and trans-beta-substituted-gamma-p-substituted-phenyl-but-3-enic acid by means of MS, IR, H-1 NMR, C-13 NMR, 2D-NOESY spectra and elemental analysis. The mechanism for the formation of products was also proposed.