140405-38-5Relevant academic research and scientific papers
Electrochemical Studies on Haloamides. Part 3. Haloacetamides and Haloacetohydroxamates
Casadei, Maria Antonietta,Rienzo, Barbara Di,Inesi, Achille,Moracci, Franco Micheletti
, p. 375 - 378 (2007/10/02)
The electrochemical reduction of haloacetamides and acetohydroxamates 1 and 2 at a mercury cathode in DMF-0.1 mol dm-3 TEAP (tetraethylammonium perchlorate) solutions has been investigated.The reduction leads to the corresponding dehalogenated products together with cyclic dimers, arising from follow-up reactions of the conjugated base of the starting compound.The same type of products, but in quite different yield, are formed when ethyl isobutyrate anion is electrogenerated in the presence of chloro derivatives 1.The reactivity of the substrates, and in particular the structure of the dimers, primarily depends on the nature of the substituent at the amide nitrogen.Possible reaction pathways leading to the products are suggested.
Electrochemical Studies on Haloamides. Part 4. Reactivity of Haloacetamides and Haloacetohydroxamates Toward Electrogenerated Diethyl Malonate Anion
Casadei, Maria Antonietta,Rienzo, Barbara Di,Inesi, Achille,Moracci, Franco Micheletti
, p. 379 - 382 (2007/10/02)
The reactivity of haloacetamides and acetohydroxamates 1 and 2 toward electrogenerated diethyl malonate anion has been investigated.The course of the reaction primarily depends on the acidity of the amide NH group, which is mainly determined by the nature of the substituent, R, at the nitrogen atom.If this substituent is the same, the nature of the halogen atom also plays an important role.If the malonate anion can act as a base, products arising from follow-up reactions of the conjugated base of the substrate are formed and their structure is dependent on R.In particular, β-lactams arising from a formal insertion of a malonate residue into the amide skeleton are obtained from haloacetanilides.When the substrate cannot be deprotonated, the diethyl malonate anion behaves as a nucleophile provided that the leaving group is bromide.Chloro derivatives are rather stable toward malonate anion.
