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1439-36-7 - (Acetylmethylene)triphenylphosphorane, 99% - 1-(Triphenylphosphoranylidene)-2-propanone - A11410 - Alfa Aesar

A11410 (Acetylmethylene)triphenylphosphorane, 99%

CAS Number
1439-36-7
Synonyms
1-(Triphenylphosphoranylidene)-2-propanone

Size Price ($) Quantity Availability
10g 39.04
50g 143.17
250g 565.20
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(Acetylmethylene)triphenylphosphorane, 99%

MDL
MFCD00008774
EINECS
215-878-2

Chemical Properties

Formula
C21H19OP
Formula Weight
318.36
Melting point
204-209°
Sensitivity
Air Sensitive
Solubility
Soluble in chloroform. Slightly soluble in methanol.

Applications

(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

Stabilized ylide which converts aldehydes to methyl ɑß-enones (see Appendix 1). Metallation with n-BuLi and alkylation, followed by Wittig reaction with an aldehyde provides a route to ɑß-unsaturated ketones: J. Org. Chem., 38, 4082 (1973); Synth. Commun., 8, 579 (1979):

For C-acylation followed by oxidation of the resulting diacylphosphoranes to give 1,2,3-triketones, see N,O-Bis(trimethyl­silyl)­acetamide, L00183.

Zhang, Y.; Wu, S.; Wang, S.; Fang, K.; Dong, G.; Liu, N.; Miao, Z.; Yao, J.; Li, J.; Zhang, W.; Sheng, C.; Wang, W. Divergent Cascade Construction of Skeletally Diverse “Privileged” Pyrazole-Derived Molecular Architectures. Eur. J. Org. Chem. 2015, 2015 (9), 2030-2037.

Chu, S.; Wallace, S.; Smith, M. D. A Cascade Strategy Enables a Total Synthesis of (-)-Gephyrotoxin. Angew. Chem. Int. Ed. 2014, 53 (50), 13826-13829.

Other References

Beilstein
750077
Harmonized Tariff Code
2931.90
TSCA
No
RTECS
UC3900000

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