Tetraethylammonium tosylate

Electrochemical reduction of the a, -unsaturated nitro compounds 32 in acetonitrile containing tetraethylammonium tosylate affords the corresponding hydrodimer in 37%... 

The oxidation of enol ethers at a reticulated vitreous carbon anode [2, 3] (Scheme 1) in a mixture of methanol/THF containing tetraethylammonium tosylate as the electrolyte and 2,6-lutidine as the base leads to substituted tetrahydrofu-ran and tetrahydropyran rings in good yields (51-96%). The major product obtained had a trans-stereochemistry. The cyclization failed to make seven-membered ring products. In order to determine the... 

Yoshida and coworkers [63, 64] studied the oxidative cycloaddition of cyclic 1,3-dione (1,3-cyclopentanedione and some 1,3-cyclohexanediones) and olefins in various solvents and electrolytes. The best results were obtained in acetonitrile containing tetraethylammonium tosylate as electrolyte (97% yield with 5,5-dimethyl-l,3-cyclohexadione and styrene) (Scheme 45). 

Two further syntheses of rose oxide (415) are described. The first is a modification of the route from citronellol (416), anodic oxidation of which (in acetonitrile with tetraethylammonium tosylate as supporting electrolyte) leads to a 71 29 mixture of ns tra s-(415). The other route is of the dihydropyran type ... 

A mixture of startg. alkyne, paraformaldehyde, and tetraethylammonium tosylate in DMF electrolyzed in the cathode compartment of a cell fitted with a Pt electrode under a constant current density of 3.3 mA/cm until 0.75 F/mol passed - product. Y 81%. Reaction is facilitated by a basic species generated in situ from paraformaldehyde, which leaves sensitive functions (epoxides and tetrahydropyranyl ethers) unaffected. F.e.s. S. Torii et al., Chem. Letters 1988, 1977-8. 

FIGURE 3 In situ ESR of electrodeposited (a) PP in CH3CN + 0.1 M tetraethylammonium tosylate and (b) PT in CHjCN + 0.1 M tetrabutylammonium perchlorate. Cyclic voltam-mograms are shown for comparison. 

Hepten-2-one electrolyzed at a cathode potential of - 2.7 v. in dioxane-methanol containing tetraethylammonium tosylate as supporting electrolyte with carbon rod electrodes and ceramic cylinder as cathode-anode diamber divider 1,2-di-methylcyclopentanol. Y 66%. F. e. s. T. Shono and M. Mitani, Am. Soc. 93, 5284 (1971) stereochemistry of electrochemical reductions, review, cf. A. J. Fry, Topics Curr. Chem. 34, 1 (1972). 

A soln. of phenylcyclopropane and tetraethylammonium tosylate as supporting electrolyte in methanol electrolyzed at room temp, with 2 carbon electrodes at 0.08 A/cm2 and 18-40 v. until 2.4 F/mole have passed l-phenyl-l,3-dimethoxy-propane. Y 74%. F. e. s. T. Shono and Y. Matsumura, J. Org. Chem. 35, 4157 (1970). 

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