Formation of Fluorinated Amido Esters through Unexpected C3−C4 Bond Fission in 4‐Trifluoromethyl‐3‐oxo‐β‐lactams |
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| Authors: | Hang Dao Thi Dr. Hannelore Goossens Dr. Dietmar Hertsen Valerie Otte Prof. Dr. Tuyen Van Nguyen Prof. Dr. Veronique Van Speybroeck Prof. Dr. Matthias D'hooghe |
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| Affiliation: | 1. SynBioC Research Group, Department of Green Chemistry and TechnologyFaculty of Bioscience Engineering, Ghent University, Ghent, Belgium;2. Institute of Chemistry, Vietnam Academy of Science and Technology, Hanoi, Vietnam;3. Center for Molecular Modeling, Ghent University, Zwijnaarde, Belgium |
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| Abstract: | 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. |
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| Keywords: | mechanism molecular modeling ring opening trifluoromethyl β -lactams |
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