Chemo- and product-selective electrooxidation of 3-(arylthiomethyl)- Δ3-cephems

Hideo Tanaka, Yoshihisa Tokumaru, Ken Ichi Fukui, Manabu Kuroboshi, Sigeru Torii, Anny Jutand, Christian Amatore

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Electrolysis of 3-arylthiomethyl-Δ3-cephems possessing various substituents on the arylthio moiety undergo chemo selective and product-selective electrooxidation to give several different products. These include isomeric mixtures of the corresponding methoxylated cephems, a bis[(Δ3-cephem-3-yl)methyl]disulfide or a 3-dimethoxymethyl- Δ3-cephem. The selectivity of the oxidation is highly dependent on the nature of the substituents on the arylthio moiety which suggests that both steric and electronic effects play an important role in the electrooxidation of 3-arylthiomethyl-Δ3-cephems.

Original languageEnglish
Pages (from-to)3449-3459
Number of pages11
JournalSynthesis
Issue number20
DOIs
Publication statusPublished - Dec 21 2009

Keywords

  • Antibiotics
  • Chemoselective
  • Electrooxidation
  • Radical cation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Tanaka, H., Tokumaru, Y., Fukui, K. I., Kuroboshi, M., Torii, S., Jutand, A., & Amatore, C. (2009). Chemo- and product-selective electrooxidation of 3-(arylthiomethyl)- Δ3-cephems. Synthesis, (20), 3449-3459. https://doi.org/10.1055/s-0029-1216972