86590-64-9Relevant articles and documents
Electrochemical Adamantylation of Styrylpyridines
Hess, U.,Huhn, D.
, p. 301 - 308 (2007/10/02)
The reaction between electrochemically generated anion radicals of the 4-(4-styryl)-pyridines 1-6 and 1-bromoadamantane gives, in solvents of low proton availability as N,N-dimethylformamide via an electron transfer in solution and formation of 1-adamantyl-radicals, monoadamantylated pyrid-4-yl-phenylethanes.The major product results from an anion radical/radical-coupling in the 2(β)-next the 1(α)-position.A competing pathway of the electrohydroadamantylation is the hydrogeneration of the -CH=CH-double bond, whose importance increases with the water content of the solvent.Based on cyclic-voltammetric evidence and product distribution, the mechanism of the reductive coupling of 1-6 in the presence of 1-bromoadamantane is discussed in terms of indirect electrolysis.