(Chloromethylene)triphenylphosphorane

Ph3P=CHCl.svg 110 px (Chloromethylene)triphenylphosphorane (Chloromethylidene)tri(phenyl)-λ5-phosphane 29949-92-6 366640 414080 1S/C19H16ClP/c20-16-21(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-16H KIZBYQRDCHVQID-UHFFFAOYSA-N C1=CC=C(C=C1)P(=CCl)(C2=CC=CC=C2)C3=CC=CC=C3 19 16 1 1 white solid (Chloromethylene)triphenylphosphorane is the organophosphorus compound with the 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.10.1002/anie.197701801 (Chloromethylene)triphenylphosphorane 1977 Appel Rolf Morbach Wolfgang Angewandte Chemie International Edition in English 16 3 180–181 (Chloromethylene)triphenylphosphorane converts aldehydes to vinyl chlorides: RCHO + Ph3P=CHCl → RCH=CHCl + Ph3PO These vinyl chlorides undergo dehydrochlorination to give alkynes:10.1002/047084289X.rc134 Chloromethyltriphenylphosphonium Chloride Encyclopedia of Reagents for Organic Synthesis 2001 Marth Charles F. 0471936235 RCH=CHCl + NaN(SiMe3)2 → RC≡CH + NaCl + HN(SiMe3)2 Related compounds (Iodomethylene)triphenylphosphoraneMathieu A. Morin Samantha Rohe Cecile Elgindy Michael S. Sherburn 10.15227/orgsyn.097.0217 Preparation of a Z-Iodoalkene through Stork-Zhao-Wittig Olefination, Stereo-retentive Lithium–iodine Exchange and Z-Boronic acid Pinacol Ester Synthesis 2020 Organic Syntheses 97 217–231 free (Dichloromethylene)triphenylphosphoraneA. J. Speziale K. W. Ratts D. E. Bissing 10.15227/orgsyn.045.0033 free Dichloromethylenetriphenylphosphoranne and β,β-Dichloro-p-dimethylaminostyrene Organic Syntheses 1965 45 33 References Category:Organophosphorus compounds