Английская Википедия:(Chloromethylene)triphenylphosphorane

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(Chloromethylene)triphenylphosphorane is the organophosphorus compound with he formula Ph3P=CHCl (Ph = phenyl). It is a white solid but is usually generated and used in situ as a reagent in organic synthesis. It is structurally and chemically related to methylenetriphenylphosphorane.

The reagent is prepared from the chloromethylphosphonium salt [Ph3PCH2Cl]Cl by treatment with strong base. The phosphonium compound is generated by treatment of triphenylphosphine with chloroiodomethane.[1]

(Chloromethylene)triphenylphosphorane converts aldehydes to vinyl chlorides:

RCHO + Ph3P=CHCl → RCH=CHCl + Ph3PO

These vinyl chlorides undergo dehydrochlorination to give alkynes:[2]

RCH=CHCl + NaN(SiMe3)2 → RC≡CH + NaCl + HN(SiMe3)2

Related compounds

  • (Iodomethylene)triphenylphosphorane[3]
  • (Dichloromethylene)triphenylphosphorane[4]

References