THE MARKOVNIKOV-ANTIMARKOVNIKOV ADDITION OF M-THIOCRESOL AND P-NITROTHLOPHENOL TO INDENE

Abstract

The addition of m-thiocresol and p-nitrothiophenol to indene has been studied under a variety of acidic conditions. The reaction of indene and m-thiocresol gave both Markovnikov and anti-Markovnikov adducts, in 58% and 42% yields, respectively. Surprisingly, in the reaction of p-nitrothiophenol and indene only the anti-Markovnikov adduct was formed. No adduct was obtained when this last reaction was run in the absence of an acid catalyst, whereas the anti-Markovnikov adduct was the only product formed in the case of m-thiocresol.