Reactions of Dichlorocarbene with Phosphorus Compounds in Low Coordination (Low σ) States

Kozo Toyota, Masaaki Yoshifuji

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1 Citation (Scopus)

Abstract

Reactions of low coordinated phosphorus compounds with dichlorocarbene and successive conversions of the resulting phosphiranes to phosphacumulenes are reviewed. Sterically protected diphosphenes reacted with dichlorocarbene to give the corresponding dichlorodiphosphiranes, which reacted with methyllithium to give 1, 3-diphosphaallenes. Similarly, the reaction of (E)-or (Z)-2-phenyl-l-(2, 4, 6-tri-t-butylphenyl)-l-phosphaethenes with dichlorocarbene afforded trans-phosphirane, which was converted to 1-phosphaallene. In some cases, the reactions of dichlorocarbene with 1-phosphaallenes, 1, 3-diphosphaallenes, or 1-phosphabutatrienes resulted in the formation of the rearranged products. Reactions of dichlorocarbene with other phosphorus species in low coordination states such as l-aza-3-phosphaallene, 1, 4-diphosphabutatriene, or phosphaalkyne are also described.

Original languageEnglish
Pages (from-to)580-588
Number of pages9
JournalJournal of Synthetic Organic Chemistry, Japan
Volume52
Issue number7
DOIs
Publication statusPublished - 1994

Keywords

  • Dichlorocarbene
  • Diphosphene
  • Low coordinated phosphorus compound
  • Main group element
  • Multiple bond
  • Phosphaalkene
  • Phosphaalkyne
  • Phosphaallene
  • Phosphacumulene
  • Steric protection

ASJC Scopus subject areas

  • Organic Chemistry

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