29834-36-4Relevant academic research and scientific papers
Electrochemical Studies on β-Lactams. Part 1. Electroreduction of 3-Halogeno-β-lactams
Casadei, Maria Antonietta,Moracci, Franco Micheletti,Inesi, Achille
, p. 419 - 424 (2007/10/02)
The electrochemical reduction in aprotic solvents of 3-halogeno-β-lactams (1a-c) and (2a-c), with or without added proton donors or/and electrophiles, has been investigated.Without added substrates, the carbanion arising from the cleavage of the carbon-halogen bond undergoes protonation (mainly from the 'parent'molecule) and, completely, ring-opening reactions yielding the corresponding dehalogenated β-lactam and α,β-unsaturated amide.In the presence of proton donors (CH3CO2H) or electrophiles (CO2), the protonation and coupling reactions, respectively, become largely predominant, and the dehalogenated or carboxylated β-lactams are the main products.In the presence of BrCH2CH2CN the protonation reaction is preferred, and the dehalogenated β-lactam predominates over the substitution product.The high yields of 3-carboxy-β-lactams, a class of compounds not easily accessible by chemical methods, are noteworthy from a synthetic point of view.
