1,1-Difluoronaphthalene-2(1H)-ones in Diels-Alder reaction

Pavel A. Zaikin, Ok Ton Dyan, Dmitry S. Fadeev, Yurii V. Gatilov, Gennady I. Borodkin

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

1,1-Difluoronaphthalene-2(1H)-ones were proposed as novel fluorinated dienophiles for the Diels-Alder reaction. The influence of the diene structure, reaction conditions on the rate and diastereoselectivity of the Diels-Alder cycloaddition was studied. For the reaction of 1,1-difluoronaphthalene-2(1H)-one with cyclopentadiene a good correlation of the logarithm of endo/exo ratio vs solvent polarity parameters were obtained. The role of diene structure and solvent effects were rationalized on the basis of DFT calculations. The factors influencing the reaction energetics were elucidated by distortion-interaction model approach. Cycloaddition-aromatization sequence was developed for the synthesis of annulated naphthalene derivatives.

Original languageEnglish
Pages (from-to)20-29
Number of pages10
JournalJournal of Fluorine Chemistry
Volume199
DOIs
Publication statusPublished - 1 Jul 2017

Keywords

  • DFT
  • Diastereoselectivity
  • Diels-Alder cycloaddition
  • Organofluorine compounds
  • Solvent effects

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