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
Publication statusPublished - Aug 2006

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Halogenation
Electrolysis
Derivatives
Nucleophiles
Platinum
Methanol
Substitution reactions
Electrodes
Complex Mixtures
Acetates
2-azetidinone

Keywords

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

ASJC Scopus subject areas

  • Electrochemistry

Cite this

Tanaka, H., Arai, S. Y., Ishitobi, Y., Kuroboshi, M., & Torii, S. (2006). Electrooxidative N-halogenation of 2-azetidinone derivatives. Electrochemistry, 74(8), 656-658.

Electrooxidative N-halogenation of 2-azetidinone derivatives. / Tanaka, Hideo; Arai, Shin Ya; Ishitobi, Yoshinori; Kuroboshi, Manabu; Torii, Sigeru.

In: Electrochemistry, Vol. 74, No. 8, 08.2006, p. 656-658.

Research output: Contribution to journalArticle

Tanaka, H, Arai, SY, Ishitobi, Y, Kuroboshi, M & Torii, S 2006, 'Electrooxidative N-halogenation of 2-azetidinone derivatives', Electrochemistry, vol. 74, no. 8, pp. 656-658.
Tanaka H, Arai SY, Ishitobi Y, Kuroboshi M, Torii S. Electrooxidative N-halogenation of 2-azetidinone derivatives. Electrochemistry. 2006 Aug;74(8):656-658.
Tanaka, Hideo ; Arai, Shin Ya ; Ishitobi, Yoshinori ; Kuroboshi, Manabu ; Torii, Sigeru. / Electrooxidative N-halogenation of 2-azetidinone derivatives. In: Electrochemistry. 2006 ; Vol. 74, No. 8. pp. 656-658.
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AU - Arai, Shin Ya

AU - Ishitobi, Yoshinori

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N2 - 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.

AB - 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.

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