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2605-67-6 - (Methoxycarbonylmethylene)triphenylphosphorane, 98% - (Carbomethoxymethylene)triphenylphosphorane - Methyl (triphenylphosphoranylidene)acetate - A14020 - Alfa Aesar

A14020 (Methoxycarbonylmethylene)triphenylphosphorane, 98%

CAS Number
2605-67-6
Synonyms
(Carbomethoxymethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate

Size Price ($) Quantity Availability
25g 85.95
100g 243.10
500g 851.20
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(Methoxycarbonylmethylene)triphenylphosphorane, 98%

MDL
MFCD00008455
EINECS
220-018-4

Chemical Properties

Formula
CH3O2CCH=P(C6H5)3
Formula Weight
334.36
Melting point
165-169°
Sensitivity
Air Sensitive
Solubility
Soluble in chloroform. Slightly soluble in ethanol and terahydrofuran. Insoluble in water.

Applications

(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

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).

For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):

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):

Review of phosphacumulene ylides: Angew. Chem. Int. Ed., 16, 349 (1977).

Dierkes, G.; Bongartz, A.; Guth, H.; Hayen, H. Quality Evaluation of Olive Oil by Statistical Analysis of Multicomponent Stable Isotope Dilution Assay Data of Aroma Active Compounds. J. Agric. Food Chem., 2012, 60 (1), 394-401.

Mears, P. R.; Thomas, E. J. Difluoroallylation using a 2-bromomethyl-1,1-difluoroalk-1-ene. Tetrahedron Lett. 2015, 56 (26), 3980-3981.

Other References

Beilstein
618430
Harmonized Tariff Code
2931.90
TSCA
Yes

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