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

22 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

Fingerprint

Fluorination
Alkenes
Organic compounds
Esters
Organophosphonates
Oxides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic α-arylthio-α-monofluorophosphonate esters. / Cao, Yi; Hidaka, Asami; Tajima, Toshiki; Fuchigami, Toshio.

In: Journal of Organic Chemistry, Vol. 70, No. 23, 11.11.2005, p. 9614-9617.

Research output: Contribution to journalArticle

@article{6a4a2e8f0ee74395946b69af4a1d8e46,
title = "Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic α-arylthio-α-monofluorophosphonate esters",
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.",
author = "Yi Cao and Asami Hidaka and Toshiki Tajima and Toshio Fuchigami",
year = "2005",
month = "11",
day = "11",
doi = "10.1021/jo051206r",
language = "English",
volume = "70",
pages = "9614--9617",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "23",

}

TY - JOUR

T1 - Electrochemical partial fluorination of organic compounds. 80. Synthesis of cyclic α-arylthio-α-monofluorophosphonate esters

AU - Cao, Yi

AU - Hidaka, Asami

AU - Tajima, Toshiki

AU - Fuchigami, Toshio

PY - 2005/11/11

Y1 - 2005/11/11

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=27744527559&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27744527559&partnerID=8YFLogxK

U2 - 10.1021/jo051206r

DO - 10.1021/jo051206r

M3 - Article

VL - 70

SP - 9614

EP - 9617

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -