Trialkylmethylammonium chlorides

Tellurium, potassium hydroxide, water, phenylacetylene, a trialkylmethylammonium chloride as phase-transfer catalyst, either tin(IJ) chloride or hydrazine hydrate as reducing agent and toluene as the organic solvent upon heating at approximately 100 for six hours produced Z,Z-bis[2-phenylvinyl ditellurium in low yields. Polytelluride radical anions were postulated as intermediates2 3. 

Z,Z)-Distyryl Tellurium2 A mixture of 12.8 g (0.1 mol) tellurium, 20.4 g (0.2 mol) phenylacetylene, 84 g (1.5 mol) potassium hydroxide, 120 ml (2.5 mol) hydrazine hydrate, 24 ml water, 40 ml toluene, and 1 g trialkylmethylammonium chloride is stirred and heated at 100 to 110° for 6 h. The mixture is diluted with water and extracted with benzene. The organic layer is washed with water, dried with potassium carbonate, filtered and the solvent evaporated from the filtrate. The residue is dissolved in diethyl ether, and the solution is poured into ethanol. After several days in the refrigerator yellow crystals of distyryl tellurium formed yield 50%. 

HPLC methods are the most convenient for determining, for example, monoalkyltri-methyl- and trialkylmethylammonium chloride impurities in dialkyldimethylammonium chloride. This analysis is described in Chapter 7. 

---