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Formation of Fluorinated Amido Esters through Unexpected C3−C4 Bond Fission in 4‐Trifluoromethyl‐3‐oxo‐β‐lactams
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2018-01-29 , DOI: 10.1002/asia.201701636
Hang Dao Thi 1, 2 , Hannelore Goossens 3 , Dietmar Hertsen 3 , Valerie Otte 1, 3 , Tuyen Van Nguyen 2 , Veronique Van Speybroeck 3 , Matthias D'hooghe 1
Affiliation  

4‐Trifluoromethyl‐3‐oxo‐β‐lactams were unexpectedly transformed into 2‐[(2,2‐difluorovinyl)amino]‐2‐oxoacetates as major products, accompanied by minor amounts of 2‐oxo‐2‐[(2,2,2‐trifluoroethyl)amino]acetates, upon treatment with alkyl halides and triethylamine in DMSO. This peculiar C3−C4 bond fission reactivity was investigated in‐depth, from both an experimental and a computational point of view, in order to shed light on the underlying reaction mechanism.

中文翻译:

通过4-三氟甲基-3-氧代-β-内酰胺中意外的C3-C4键裂变形成氟化酰胺基酯

4-三氟甲基-3-氧代-β-内酰胺意外地转化为2-[((2,2-二氟乙烯基)氨基] -2-氧代乙酸酯作为主要产物,并伴有少量的2-氧代-2-[[2, 2,2-三氟乙基)氨基]乙酸酯,在DMSO中用卤代烷和三乙胺处理。从实验和计算的角度对这种奇特的C3-C4键裂变反应性进行了深入研究,以阐明潜在的反应机理。
更新日期:2018-01-29
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