Electrooxidative N-halogenation of 2-azetidinone derivatives

Hideo Tanaka, Shin Ya Arai, Yoshinori Ishitobi, Manabu Kuroboshi, Sigeru Torii

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Electrolysis of 2-azetidinone 3 in AcOH/CH3CN containing NaBr (2-10 equiv.) was carried out in an undivided cell fitted with two platinum electrodes to afford the corresponding N-bromo-2-azetidinones 2a, while a similar electrolysis in a divided cell afforded no appreciable amount of 2 but a small amount of 4-acetoxy-2-azetidinone 1 together with a complex mixture. Ring-expansion of 2-azetidinone 3 leading to 4 took place exclusively by electrolysis in methanol containing AcONa. On the other hand, N-iodination proceeded efficiently only in a divided cell in the presence of 2.5 equiv. of NaI. Reaction of N-bromo-2-azetidinone 2 with various nucleophiles, e.g., acetate, thiolate, and alkoxides, afforded no substitution products, resulting in the reductive debromination leading to 3, whereas with diphenyl disulfide, N-phenylsulfenyl-2-azetidinone 5 was mainly obtained.

Original languageEnglish
Pages (from-to)656-658
Number of pages3
JournalElectrochemistry
Volume74
Issue number8
DOIs
Publication statusPublished - Aug 2006

Keywords

  • Azetidinone
  • Electrooxidation
  • N-Halogenation
  • β-Lactam Antibiotics

ASJC Scopus subject areas

  • Electrochemistry

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