Selective preparation of 1-substituted 2,2-difluoroethenyl phosphates or 1-hydroxyalkanephosphonates through the reaction of chlorodifluoromethyl ketones with dialkyl or diaryl phosphites

Takashi Ishihara, Masayuki Yamana, Takashige Maekawa, Manabu Kuroboshi, Teiichi Ando

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Various chlorodifluoromethyl ketones react readily with dialkyl or diaryl phosphites in the presence of triethylamine at the reflux temperature of tetrahydrofuran to give the corresponding dialkyl or diaryl 1-substituted-2,2-difluoroethenyl phosphates in good yields, whereas the similar reaction conducted at lower temperature (0-20 °C) affords 1-(chlorodifluoromethyl)-1-hydroxyalkanephosphonates almost exclusively. The latter compounds are converted to the former enol phosphates by the treatment with triethylamine or sodium methoxide in refluxing tetrahydrofuran.

Original languageEnglish
Pages (from-to)263-277
Number of pages15
JournalJournal of Fluorine Chemistry
Volume38
Issue number2
DOIs
Publication statusPublished - 1988
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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