Reduction of unsymmetrical benzils using sodium dithionite

SM Heilmann, JK Rasmussen…

Index: Heilmann, Steven M.; Rasmussen, Jerald K.; Smith, Howell K. Journal of Organic Chemistry, 1983 , vol. 48, # 7 p. 987 - 992

Full Text: HTML

Citation Number: 17

Abstract

Contrary to a previous report, reduction of unsymmetrical benzils by sodium dithionite (sodium hydrosulfite) in general yields a mixture of isomeric benzoins. Whereas the reduction of aldehydes and ketones by dithionite apparently takes place by a nucleophilic addition mechanism, the reduction of benzils proceeds by an electron-transfer mechanism. The inital product of the reduction is the (aa, a'-stilbenediol which is produced ...