2005•Organic LettersOpen access

Superacid-Catalyzed Reactions of Olefinic Pyrazines: an Example of Anti-Markovnikov Addition Involving Superelectrophiles

Yiliang Zhang, Jason Briski, Yun Zhang, Rendy Rendy, Douglas A. Klumpp

Abstract

[reaction: see text] Olefinic pyrazines are found to react with benzene in CF3SO3H and give anti-Markovnikov-type addition products. We propose that this is caused by two effects: destabilization of the carbocationic intermediates that would lead to Markovnikov-type products and the generation of a considerable amount of positive charge at the terminal carbon of the olefinic groups. This suggests that acid-catalyzed addition reactions can give anti-Markovnikov-type products when a multiply charged (i.e., superelectrophilic) group is adjacent to the olefinic site.

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Available abstract

Key concepts: Markovnikov's rule, Chemistry, Superacid, Catalysis, Benzene, Organic chemistry, Medicinal chemistry, Regioselectivity