(Methoxycarbonylmethylene)triphenylphosphorane

• Catalog No.: A14020
• CAS Number: 2605-67-6
• M. F.: C21H19O2P
• M. W.: 334.348121
• Purity: 98%

SYNONYMS

• Title: (甲氧基羰基亚甲基)三苯基膦烷
• IUPAC name: methyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• IUPAC Traditional name: methyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• Synonyms: (Carbomethoxymethylene)triphenylphosphorane; Methyl (triphenylphosphoranylidene)acetate

DATABASE IDS

• MDL Number: MFCD00008455
• Beilstein Number: 618430
• EC Number: 220-018-4
• CAS Number: 2605-67-6

PROPERTIES

• Purity: 98%
• Melting Point: 165-169°C
• Storage Warning: Air Sensitive
• TSCA Listed: 是

REFERENCES

• For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):
  
• Review of phosphacumulene ylides: Angew. Chem. Int. Ed.,16, 349 (1977).
• Stable ylide which undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. See also (Ethoxycarbonylmethylene)triphenylphosphorane, A12896 and Appendix 1. For a detailed study of the reaction with benzaldehyde, see J. Org. Chem., 59, 1126 (1994). For use of high pressure to increase the yield and trans-selectivity of reaction with aromatic aldehydes, see: Liebigs Ann. Chem., 2135 (1983).
• Strong base, for example Na bis(TMS)amide, brings about elimination of methanol, giving ketenylidenetriphenylphosphorane, which reacts with ɑ-hydroxy-ketones, e.g. in the steroid series, to give butenolides, by acylation and Wittig cyclization: Chem. Ber., 113, 2038 (1980):