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

A14020 (Methoxycarbonylmethylene)triphenylphosphorane, 98%

Número CAS
2605-67-6
Nombre Alternativo
(Carbomethoxymethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate

Tamaño Precio ($) Cantidad Disponibilidad
25g 85,95
100g 243,10
500g 851,20
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(Methoxycarbonylmethylene)triphenylphosphorane, 98%

MDL
MFCD00008455
EINECS
220-018-4

Propiedades químicas

Fórmula
CH3O2CCH=P(C6H5)3
Peso molecular
334.36
Punto de fusión
165-169°
Sensibilidad
Air Sensitive
Solubilidad
Soluble in chloroform. Slightly soluble in ethanol and terahydrofuran. Insoluble in water.

Aplicaciones

(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.

Notas

Air sensitive. Incompatible with strong oxidizing agents.

Referencias documentales

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.

Otras referencias

Beilstein
618430
Código de tarifa arancelaria unificado
2931.90
TSCA
Yes

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