Journal of Flow Chemistry ( IF 2.7 ) Pub Date : 2020-02-14 , DOI: 10.1007/s41981-019-00057-6 Baptiste Picard , Katia Pérez , Thomas Lebleu , Daniela Vuluga , Fabrice Burel , David C. Harrowven , Isabelle Chataigner , Jacques Maddaluno , Julien Legros
The generation and reactivity of two model vinyl carbenoids from gem-dibromoalkenes 1 were studied in microflow systems. From substrate 1a (R = Ph, CF3), the lithium-bromine exchange could be simply performed within 30 ms at 20 °C with very good E-selectivity whereas the reaction was unselective under batch conditions, even at −78 °C. Moreover, the unstable carbenoid generated from 1b (R = Ph, H) could be trapped as the major product while only the Fritsch-Buttemberg-Wiechell rearrangement product was obtained in a flask under cryogenic conditions.
中文翻译:
宝石-二溴烯烃上的溴-锂交换第1部分:批次与微流条件
在微流系统中研究了两种来自宝石-二溴烯烃1的模型乙烯基类胡萝卜素的生成和反应性。从底物1a(R = Ph,CF 3),锂-溴交换可以简单地在20 ms的30毫秒内以非常好的E选择性进行,而在间歇条件下,即使在-78°C,反应也是非选择性的。此外,从1b(R = Ph,H)生成的不稳定类胡萝卜素可以被捕集为主要产物,而在低温条件下只能在烧瓶中获得Fritsch-Buttemberg-Wiechell重排产物。