Triphenyl sodium cyanide

Triphenyl Tellurium Cyanide1 20 g of a Baker CHA-541 resin are treated with aqueous sodium cyanide solution, the column is washed with ethanol/water mixtures with increasing ethanol content, and, finally, the column is covered with 95% ethanol. A solution of 0.1 g (2.5 mmol) of triphenyl telluronium chloride in 60 ml of 95% ethanol is slowly passed through the column. The column is eluted with 200 ml of ethanol, the cluate is evaporated, the oily residue is triturated with ethyl acetate, and the crystals are collected, washed with ethyl acetate, and dried under vacuum yield 0.82 g (85%) m.p. 184° (dec.). 

In 1896, Lottermoser reported243 that in the presence of sodium, benzonitrile in refluxing benzene produces 2,2,4,6-tetraphenyl- 1,2-dihydro-1,3,5-triazine (157), sodium cyanide, and 2,4,6-triphenyl-1,3,5-triazine (153) [Eq (71)]. 

KETONES f-Butyl a-lithioisobutyrate. Benzoin. Chlorocarbonylbis(triphenylphosphine)-rhodium(I). m-Chloroperbenzoic acid. Chromic acid. Dimethylcopperlithium. Diphenyl disulfide. Formaldehyde diphenyl thioacetal. Methylthioacetic acid. Sodium cyanide. Tetrakis triphenylphosphine)palladium(0). Trimethylchlorosilane. Triphenyl-methyl isocyanide. Trimethylsilyl cyanide. 

A number of general methods for the synthesis of meso-ionic 1,2,4-triazol-3-ones are available. Sodium ethoxide-catalyzed cyclization of 1-benzoyl-l,4-diphenylsemicarbazide (201, R = R = R = Ph, X = O) yielded anhydro-3-hydroxy-1,4,5-triphenyl-1,2,4-triazolium hydroxide (200, R = R = R = Ph). A general route to meso-ionic 1,2,4-triazol-3-ones (200) is exemplified by the formation of the 1,4,5-triphenyl derivative (200, R = R = R = Ph) from A-amino-MA -diphenylbenzamidine (202, R = R = R = Ph) and phosgene. In contrast with this ready meso-ionic compound formation, the corresponding reaction of the iV-methylbenzamidine (202, R = Me, R = R = Ph) did not yield the meso-ionic 1,2,4-triazol-3-one (200, R = Me, R = R = Ph). The product was in fact 3,4-diphenyl-2-methyl-l,2,4-triazol-5-onium chloride (203), which on heating gave 3,4-diphenyl-1,2,4-triazol-5-one (204, R = Ph). The formation of the A-methyl derivative (200, R = Me, R = R = Ph, yield 79%) by heating the 7V-thiobenzoyl semicarbazide (201, R = Me, R = R = Ph, X = S) with potassium carbonate in methyl cyanide has been reported. Another synthesis of A-methyl derivatives (200, R = Me) involves methylation of 3-methyl-4-phenyl-l,2,4-triazol-5-one (204,... 

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