Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes to Generate Alkenes

Article abstract of DOI:10.1021/jo9716901

β-Nitrostyrenes 1 react with trialkylboranes under a nitrogen atmosphere to generate high yields of alkenes 2. The mechanism is proposed to be a free-radical reaction via NO₂/alkyl substitution since the reaction is stimulated by the presence of a trace of oxygen in the nitrogen or tert-butyl peroxide or by photolysis and is retarded or inhibited by the addition of galvinoxyl to the solution.