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Formation of fluorinated amido esters through unexpected C3-C4 bond fission in 4-trifluoromethyl-3-oxo-β-lactams

(2018) CHEMISTRY-AN ASIAN JOURNAL. 13(4). p.421-431
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Abstract
4-Trifluoromethyl-3-oxo--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.
Keywords
mechanism, molecular modeling, ring opening, trifluoromethyl, -lactams, DENSITY-FUNCTIONAL THEORY, ALPHA-AMINO-ACIDS, 3-SUBSTITUTED 3-HYDROXY-BETA-LACTAMS, STEREOSELECTIVE-SYNTHESIS, NONCOVALENT INTERACTIONS, THERMOCHEMICAL KINETICS, SELECTIVE METHOD, BETA-LACTAMS, AZETIDINE-2, 3-DIONES, TRIFLUOROMETHYLATION

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Citation

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Chicago
Dao, Thi Hang, Hannelore Goossens, Dietmar Hertsen, Valerie Otte, Tuyen Van Nguyen, Veronique Van Speybroeck, and Matthias D’hooghe. 2018. “Formation of Fluorinated Amido Esters Through Unexpected C3-C4 Bond Fission in 4-trifluoromethyl-3-oxo-β-lactams.” Chemistry-an Asian Journal 13 (4): 421–431.
APA
Dao, T. H., Goossens, H., Hertsen, D., Otte, V., Van Nguyen, T., Van Speybroeck, V., & D’hooghe, M. (2018). Formation of fluorinated amido esters through unexpected C3-C4 bond fission in 4-trifluoromethyl-3-oxo-β-lactams. CHEMISTRY-AN ASIAN JOURNAL, 13(4), 421–431.
Vancouver
1.
Dao TH, Goossens H, Hertsen D, Otte V, Van Nguyen T, Van Speybroeck V, et al. Formation of fluorinated amido esters through unexpected C3-C4 bond fission in 4-trifluoromethyl-3-oxo-β-lactams. CHEMISTRY-AN ASIAN JOURNAL. 2018;13(4):421–31.
MLA
Dao, Thi Hang, Hannelore Goossens, Dietmar Hertsen, et al. “Formation of Fluorinated Amido Esters Through Unexpected C3-C4 Bond Fission in 4-trifluoromethyl-3-oxo-β-lactams.” CHEMISTRY-AN ASIAN JOURNAL 13.4 (2018): 421–431. Print.
@article{8544829,
  abstract     = {4-Trifluoromethyl-3-oxo--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.},
  author       = {Dao, Thi Hang and Goossens, Hannelore and Hertsen, Dietmar and Otte, Valerie and Van Nguyen, Tuyen and Van Speybroeck, Veronique and D'hooghe, Matthias},
  issn         = {1861-4728},
  journal      = {CHEMISTRY-AN ASIAN JOURNAL},
  language     = {eng},
  number       = {4},
  pages        = {421--431},
  title        = {Formation of fluorinated amido esters through unexpected C3-C4 bond fission in 4-trifluoromethyl-3-oxo-\ensuremath{\beta}-lactams},
  url          = {http://dx.doi.org/10.1002/asia.201701636},
  volume       = {13},
  year         = {2018},
}

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