Formation of Fluorinated Amido Esters through Unexpected C3-C4 Bond Fission in 4-Trifluoromethyl-3-oxo-[beta]-lactams

4-Trifluoromethyl-3-oxo-[beta]-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...

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Bibliographic Details
Published inChemistry, an Asian journal Vol. 13; no. 4; p. 421
Main Authors DaoThi, Hang, Goossens, Hannelore, Hertsen, Dietmar, Otte, Valerie, VanNguyen, Tuyen, VanSpeybroeck, Veronique, D'hooghe, Matthias
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 16.02.2018
Subjects
Acetates
Actuarial cost methods
Chemistry
Esters
Fission
Fluorination
Halides
Reaction mechanisms
Triethylamine
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Summary:4-Trifluoromethyl-3-oxo-[beta]-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.
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201701636