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

A14020 (Methoxycarbonylmethylene)triphenylphosphorane, 98%

Codice CAS
2605-67-6
Sinonimi
(Carbomethoxymethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate

Dimensioni Prezzo ($) Quantità Disponibilità
25g 89,90
100g 259,00
500g 1043,00
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(Methoxycarbonylmethylene)triphenylphosphorane, 98%

MDL
MFCD00008455
EINECS
220-018-4

Proprietà chimiche

Formula
CH3O2CCH=P(C6H5)3
Peso formula
334.36
Punto di fusione
165-169°
Sensibilità
Air Sensitive
Solubilità
Soluble in chloroform. Slightly soluble in ethanol and terahydrofuran. Insoluble in water.

Applicazioni

(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.

Note

Air sensitive. Incompatible with strong oxidizing agents.

Letteratura

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.

Altri riferimenti

Beilstein
618430
Codice tariffe armonizzato
2931.39
TSCA
Yes

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