Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles |
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Authors: | Zhang Yiliang Briski Jason Zhang Yun Rendy Rendy Klumpp Douglas A |
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Affiliation: | Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA. |
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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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