Reactions of haloarenes, haloheteroarenes and dihalobenzenes with triphenylstannyl anions in DMSO and acetonitrile
作者:Marı́a T. Lockhart、Alicia B. Chopa、Roberto A. Rossi
DOI:10.1016/s0022-328x(99)00040-6
日期:1999.6
react with Ph3Sn− ions faster by an HME mechanism than by the SRN1 process. In the photostimulated reaction of 1-chloronaphthalene, 2-chloro and 3-chloropyridines with Ph3Sn− ions in DMSO, the substitution products are obtained in 72, 82 and 93% yields, respectively. With p-dichlorobenzene the di-substitution product is obtained in 90% yield. All these reactions occur by the SRN1 mechanism. Yields improve
我们研究了不同的卤代芳烃,haloheteroarenes和二卤代苯的Ph 3 Sn的-在DMSO或乙腈(CH离子3 CN)作为溶剂,在黑暗中或在照射下,以确定是否卤素金属交换(HME)反应或在S RN 1过程的获胜。用对氯苯甲醚在DMSO中光刺激的反应缓慢。存在与2-和3-氯噻吩的HME反应。Bromoarenes(p -bromoanisole,p二溴苯和1-溴萘)和p -iodoanisole的Ph反应3的Sn -由S快离子通过HME机构比RN1个过程。在1-氯萘的光刺激反应,2-氯和3-氯吡啶的Ph 3 Sn的-在DMSO中的离子,所述取代产物在72,82和93%的收率分别获得。用对-二氯苯以90%的产率获得二取代产物。所有这些反应都是通过S RN 1机制发生的。当反应在DMSO而不是在CH 3 CN中进行时,产率提高。