SEARCH

SEARCH BY CITATION

Keywords:

  • cyclization;
  • domino reactions;
  • rearrangement;
  • spiro compounds;
  • thermochemistry
Thumbnail image of graphical abstract

Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.