- Reduction of Unsymmetrical Benzils Using Sodium Dithionite
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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 initial product of the reduction is the (Z)-α,α'-stilbenediol which is produced stereospecifically.The ultimate benzoin products, then, result from the two different modes of ketolization of the stilbenediol intermediate.
- Heilmann, Steven M.,Rasmussen, Jerald K.,Smith, Howell K.
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p. 987 - 992
(2007/10/02)
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