Highly efficient, catalytic bis addition reactions of allyl phenyl sulfone to vinyl sulfones

Highly efficient, electrocatalytic additions of allyl phenyl sulfone to a variety of vinyl sulfones have been accomplished. The additions are catalyzed by electrogenerated bases derived from the reactant itself, and furnish 90-94% yields of highly polar molecules in which 1 mol of allyl phenyl sulfone has added consecutively, selectively, and in a linear addition mode to 2 mol of the vinyl sulfone. Essentially no products are observed which incorporate other than 2 mol of the vinyl sulfone. Ail addition to a difunctional alkene, divinylsulfone, yields a novel cyclization product, albeit in more moderate yield (41%). The use of tetraalkyl-ammonium salts. as opposed to lithium salts, as electrolytes has been found to provide electrogenerated bases of especially high reactivity. (C) 2004 Elsevier Ltd. All rights reserved.