Chemistry:(Chloromethylene)triphenylphosphorane
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| Preferred IUPAC name
(Chloromethylidene)tri(phenyl)-λ5-phosphane | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C19H16ClP | |
| Molar mass | 310.76 g·mol−1 |
| Appearance | white solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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
References
- ↑ Appel, Rolf; Morbach, Wolfgang (1977). "(Chloromethylene)triphenylphosphorane". Angewandte Chemie International Edition in English 16 (3): 180–181. doi:10.1002/anie.197701801.
- ↑ Marth, Charles F. (2001). "Chloromethyltriphenylphosphonium Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc134. ISBN 0471936235.
- ↑ Morin, Mathieu A.; Rohe, Samantha; Elgindy, Cecile; Sherburn, Michael S. (2020). "Preparation of a Z-Iodoalkene through Stork-Zhao-Wittig Olefination, Stereo-retentive Lithium–iodine Exchange and Z-Boronic acid Pinacol Ester Synthesis". Organic Syntheses 97: 217–231. doi:10.15227/orgsyn.097.0217.
- ↑ Speziale, A. J.; Ratts, K. W.; Bissing, D. E. (1965). "Dichloromethylenetriphenylphosphoranne and β,β-Dichloro-p-dimethylaminostyrene". Organic Syntheses 45: 33. doi:10.15227/orgsyn.045.0033.
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