Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic alpha-arylthio-alpha-monofluorophosphonate esters.
[Reaction: see text]. Seven-membered cyclic alpha-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 alpha-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.
Cao
Yi
Y
Department of Electric Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama, 226-8502, Japan.
Hidaka
Asami
A
Tajima
Toshiki
T
Fuchigami
Toshio
T
D003500:Cyclization; D004563:Electrochemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*
D004952:Esters; D063065:Organophosphonates; D005461:Fluorine