Photochemical Generation and Reactivity of Naphthyl Cations: cine Substitution

M. Slegt, F. Minne, H. Zuilhof, H.S. Overkleeft, G. Lodder

Research output: Contribution to journalArticleAcademicpeer-review

11 Citations (Scopus)

Abstract

The photochemical solvolyses of naphthalen-1-yl(phenyl)iodonium tetrafluoroborate and naphthalen-2-yl(phenyl)iodonium tetrafluoroborate in methanol regiospecifically yield the naphthalen-1- and -2-yl ethers but afford scrambled 1- and 2-phenylnaphthalene Friedel-Crafts products. It is demonstrated that singlet naphthyl cations account for the formation of the naphthyl ethers, but that the cine substitution is most likely to be due to the intermediacy of triplet naphthyl cations. According to the experiments reported here, the singlet naphthyl cations are lower in energy than their triplet isomers. High-level MO calculations for the cations in methanol support this finding.
Original languageEnglish
Pages (from-to)5353-5363
JournalEuropean Journal of Organic Chemistry
Volume2007
Issue number32
DOIs
Publication statusPublished - 2007

Keywords

  • polycyclic aromatic-hydrocarbon
  • aryl cations
  • interstellar chemistry
  • iodonium salts
  • phenyl cations
  • naphthalene
  • ion
  • tetrafluoroborate
  • elimination
  • molecules

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