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Synthesis 1986; 1986(7): 591-593
DOI: 10.1055/s-1986-31719
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Electrochemical Studies of ß-Lactams; Part 21. Electrosynthesis of ß-Lactams via Bond Formation between C-3 and C-4

Italo Carelli* , Achille Inesi, Vincenzo Carelli, Maria Antonietta Casadei, Felice Liberatore, Franco Micheletti Moracci
  • *Centro per l'Elettrochimica e la Chimica Fisica delle Interfasi del CNR, Roma, Italy
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Publication Date:
20 August 2002 (online)

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An electrochemical synthesis of ß-lactams from readily available substituted haloacetamides is reported. The formation of an anionic site, which promotes cyclization by intramolecular nucleophilic substitution, occurs either directly on the substrate molecule by electrochemical reduction of a carbon-halogen bond, or following induction on the substrate itself by a base, also generated by electroreduction of a suitable probase. The procedure is characterized by high yields and versatility, and its compatibility with sensitive groups present in the substrate molecules.