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Keywords:

  • Arene formation;
  • Cyclization reactions;
  • Salicylates;
  • Organochlorine compounds;
  • Silyl enol ethers

Abstract

A variety of 6-(trichloromethyl)salicylates (=2-hydroxy-6-(trichloromethyl)benzoates) were prepared by TiCl4-mediated cyclization of 1,3-bis(trimethylsilyloxy)buta-1,3-dienes with 1,1,1-trichloro-4,4-dimethoxybut-3-en-2-one. The employment of trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) as Lewis acid resulted in the formation of trichloromethyl-substituted cyclohexenones. The cyclizations proceeded with good-to-very-good regioselectivities.