140480-04-2Relevant academic research and scientific papers
Reduction of flavanones by NaBH3CN in trifluoroacetic acid.
Lewin, G.,Bert, M.,Dauguet, J. C.,Dolley, J.,Menez, P. Le,et al.
, p. 939 - 944 (2007/10/02)
For our studies on the reduction of flavanones, we worked on flavanone itself and on some other derivatives, oxygenated on the B ring.Besides expected flavans and chalcanes, condensed compounds (dimers and trimers) are also obtained.Reaction begins with the reduction of carbonyl to methylene; all the other isolated products arise from the two possible and competitive reactions on the potential carbocation C-2 of the flavan system: a) reductive cleavage of heterocycle; b) electrophilic aromatic substitution.Reactivity of flavanones is correlated with substituents of B ring through their ?+ values. Key words: flavanones / sodium cyanoborhydride / trifluoroacetic acid / flavans / chalcanes / dimers
