Highly efficient, catalytic bis addition reactions of allyl phenyl sulfone to vinyl sulfones |
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Authors: | Greg AN Felton |
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Institution: | Department of Chemistry and Biochemistry, The University of Texas, Austin, TX 78712, USA |
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Abstract: | 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. An addition to a difunctional alkene, divinylsulfone, yields a novel cyclization product, albeit in more moderate yield (41%). The use of tetraalkylammonium salts, as opposed to lithium salts, as electrolytes has been found to provide electrogenerated bases of especially high reactivity. |
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Keywords: | Catalytic Electrogenerated base Bis addition Allyl vinyl sulfone Phenyl vinyl sulfone Cyclization |
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