Solvent-free Michael addition of 2-cyclohexenone under ultrasonic irradiation in the presence of long chain dicationic ammonium salts

Öge A., Maviş M. E., Yolaçan Ç., Aydoğan F.

TURKISH JOURNAL OF CHEMISTRY, vol.36, pp.137-146, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 36
  • Publication Date: 2012
  • Doi Number: 10.3906/kim-1104-63
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.137-146
  • Yıldız Technical University Affiliated: Yes


Long chain dicationic ammonium salts (1a-1c), easily prepared from tert-amines and dihaloalkanes, were successfully used as efficient phase-transfer catalysts in the Michael addition reaction of various active methylene compounds to 2-cyclohexenone without solvent under ultrasonic irradiation. The investigated dicationic salts were more effective than monocationic tetrabutylammonium bromide, with short reaction times and high yields. This methodology was established under phase-transfer catalytic conditions and ultrasonic effects with many advantages, including the easy and cost-effective synthesis of the catalyst, mild reaction conditions, short reaction times, good yields, simple work-up procedures. and environmental friendliness.