Novel Chemoselective Reduction of Aldehydes in the Presence of Other Carbonyl Moieties with Thiourea Dioxide

Abstract

Reduction of a variety of aldehydes in the presence of other carbonyl moieties to the corresponding alcohols occurs chemoselectively in high yields upon treatment with inexpensive reagent thiourea dioxide (TUDO) in aqueous alkali–ethanolic system for 2 h at 90 °C.

Keywords:

• Aldehyde
• Carbonyl
• Chemoselective
• Formamidine sulfinic acid
• Reduction
• Thiourea dioxide

ACKNOWLEDGMENT

The authors thank University Grants Commission (UGC), New Delhi, for financial support.

Notes

^a The unreacted ketones were isolated almost in quantitative yield.

^b Products were characterized by comparison (mp/bp, TLC, GLC, IR, and ¹H NMR) with authentic samples

^c No condensation or Cannizaro's products were detected from the reaction mixture

^d Aldehyde: Carbonyls: TUDO

^e Isolated yield.

Part of this work was presented at the IUPAC Second International Symposium on Green/Sustainable Chemistry, University of Delhi, New Delhi, India, January 10–13, 2006.