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Synthesis, Reactivity, and Antibacterial Activity of gem-Difluoroalkene, Difluoromethyl, and Trifluoromethyl β-Lactams.

ABSTRACT: New gem-difluoroalkenes were synthesized by the dehydrofluorination of the corresponding 4-CF₃-β-lactams. An unexpected rearrangement mechanism of the ester moiety dependent on a stabilizing negative charge was observed. Hydrogenation to 4-CHF₂-β-lactams was successful from gem-difluoro-β-lactams.

SUBMITTER: Skibinska M

PROVIDER: S-EPMC10825868 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Synthesis, Reactivity, and Antibacterial Activity of gem-Difluoroalkene, Difluoromethyl, and Trifluoromethyl β-Lactams.

Skibinska Monika M Warowicka Alicja A Koroniak Henryk H Cytlak Tomasz T Crousse Benoît B

Organic letters 20240116 3

New gem-difluoroalkenes were synthesized by the dehydrofluorination of the corresponding 4-CF3-β-lactams. An unexpected rearrangement mechanism of the ester moiety dependent on a stabilizing negative charge was observed. Hydrogenation to 4-CHF2-β-lactams was successful from gem-difluoro-β-lactams. ...[more]

PMID: 38227548

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