Hexaethyl phosphorous triamide is used in the Barton syntheses of hindered alkenes, involving desulfurization of small-ring heterocycles with elimination of nitrogen or carbon dioxide. It is also used as a reagent for selective vicinal dehalogenation of halogenated alkanes to give perhalogenated alkenes. The method has potential for the synthesis of highly fluorinated and mixed fluoro-halo alkenes.
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Applications
Hexaethyl phosphorous triamide is used in the Barton syntheses of hindered alkenes, involving desulfurization of small-ring heterocycles with elimination of nitrogen or carbon dioxide. It is also used as a reagent for selective vicinal dehalogenation of halogenated alkanes to give perhalogenated alkenes. The method has potential for the synthesis of highly fluorinated and mixed fluoro-halo alkenes.
Solubility
Insoluble in water.
Notes
Keep container tightly sealed. Store in cool, dry conditions in well sealed containers. Incompatible with oxidizing agents. It is sensitive to air. Store under dry inert gas.
RUO – Research Use Only
Theodor Reetz. Trialkyl Phosphite Borines. A New Type of Phosphorus-boron Compound. J. Am. Chem. Soc. 1960, 82, (19), 5039-5042.
Liming Jiang.; Zhiquan Shen.; Yuhui Yang.; Yifeng Zhang. Synthesis of ultra-high molecular weight polystyrene with rare earth-magnesium alkyl catalyst system: general features of bulk polymerization. Polymer International. 2001, 50 (1), 63-66.
Reducing agent, compare Hexamethylphosphorous triamide, A12571.
For use in the Barton syntheses of hindered alkenes, involving desulfurization of small-ring heterocycles with elimination of nitrogen or carbon dioxide, see: Chem. Commun., 1225, 1226 (1970):
Reagent for selective vicinal dehalogenation of halogenated alkanes to give perhalogenated alkenes. The method has potential for the synthesis of highly fluorinated and mixed fluoro-halo alkenes: J. Org. Chem., 57, 5018 (1992).