Triphenyl sodium azide

From Sodium Azide and Vinylphosphonium Salts Phosphonium salts of the types 4 and 5 react with sodium azide in aqueous solution to give v-triazoles in high yield. The proposed mechanism (Scheme 13) involves nucleophilic attack at the carbon jS-tothe phosphorus, followed by cyclization with displacement of triphenyl-phosphine. 

Triphenyl Telluronium Azide1 A solution of 2.6 g (40 mmol) sodium azide in 100 ml of water is shaken with a solution of 2.0 g (5 mmol) of triphenyl telluronium chloride in 200 ml of chloroform. The organic layer is separated, dried with anhydrous magnesium sulfate, filtered, and the filtrate concentrated to a volume of 40 ml. The concentrate is cooled and slowly mixed with cold petroleum ether (b.p. 30-60°), and the precipitate is filtered off yield 1.5 g (80%) m.p. 165° (from toluene). 

AZIRIDINES Lead tetraacetate. Sodium azide-Triphenylphosphine. Triphenyl-phosphine-Diethyl azodicarboxylate. 

A valuable route to benzofurazans is provided by deoxygenation of the corresponding benzofuroxan. This may be accomplished either directly using trialkyl phosphites, tributyl-or triphenyl-phosphine, or indirectly via the quinone dioxime using, for example, methanol and potassium hydroxide, hydroxylamine and alkali, sodium azide in DMSO or ethylene glycol, sodium borohydride, and occasionally thermolysis alone. More detailed discussion of these reactions is included in Section 4.22.3.2.4. 

As electro positivity increases, the azides of the heavier IV A elements shift toward a more hydrophile behavior. This pattern is qualitatively noticeable in the triorganyl element azides (see Table XFV for trimethyl compounds). The triphenyl compounds display a similar behavior [9,261,272]. Basically, all R3E1(N3) compounds are accessible from the respective chloro compounds and sodium azide in ether/water media [273]. 

Treatment of enecarbamate 344 with sodium azide and ceric ammonium nitrate (CAN) in acetone furnished azidocarbazole 345. The low yield in this oxidative cychzation reaction is due to formation of the diastereomer consisting of stereochemical inversion at the azide-substituted carbon. At this point, azide reduction employing the Staudinger conditions of triphenyl-phosphine in a mixture of water and THF led to an amine, which was subjected to trichloroacetyl chloride in a solution of dichloromethane and triethylamine to yield amide 346 (Scheme 49). 

Related Reagents. Bromine-r-Butylamine Bromine Chloride Bromine-l,4-Diazabicyclo[2.2.2]octane Bromine-1,4-Dioxane Bromine-Silver(I) Oxide Bromine-Triphenyl Phosphite iV-Bromosuccinimide A7-Bromosiiccinimide-Dimethylformamide 7V-Bromosuccinimide-Dimethyl Sulfide Al-Bromosuccinimide-Sodium Azide Copper(II) Bromide Hy-drobromic Acid Mercury(II) Oxide-Bromine Phosphoms(III) Bromide Pyridinium Hydrobromide Perbromide Sodium Bromide Thallium(III) Acetate-Bromine. 

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