Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic α-arylthio-α-monofluorophosphonate esters

Yi Cao, Asami Hidaka, Toshiki Tajima, Toshio Fuchigami

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Seven-membered cyclic α-monofluorophosphonate esters such as 2-allyloxy-3-fluoro-3-phenylthio-4,7-dihydro-[1, 2]-oxaphosphinine-2-oxide were successfully synthesized in moderate total yield as 41% from open-chain allyl phosphonates having an α-arylthio group as an electroauxiliary using an alternative sequence of anodic fluorination and ring-closing olefin metathesis (RCM). On the other hand, in an attempt to synthesize an eight-membered analogue, a different type of seven-membered fluorinated cyclic product was formed predominantly by the RCM reaction between the allyloxy groups.

Original languageEnglish
Pages (from-to)9614-9617
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number23
DOIs
Publication statusPublished - 2005 Nov 11
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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