title: Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: mechanisms correlated to charge distributions.
abstract: The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.
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: Matthew R
authors.initials: MR
authors.lastname: Sheets
authors.forename: Erum K
authors.initials: EK
authors.lastname: Raja
authors.forename: Kenneth N
authors.initials: KN
authors.lastname: Boblak
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
mesh_terms: D000143:Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry*; D011810:Quinoxalines / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000143:Acids; D011743:Pyrimidines; D011799:Quinazolines; D011810:Quinoxalines; D014753:Vinyl Compounds