title: Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles.
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.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA.
authors.forename: Yiliang
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jason
authors.initials: J
authors.lastname: Briski
authors.forename: Yun
authors.initials: Y
authors.lastname: Zhang
authors.forename: Rendy
authors.initials: R
authors.lastname: Rendy
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001554:Benzene / Q000737:chemistry; D002384:Catalysis; D004563:Electrochemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007202:Indicators and Reagents; D011719:Pyrazines; D001554:Benzene