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Reductive homocoupling of acetals derived from aromatic aldehydes with aluminium/lead bimetal redox system
Dhimane, H.,Tanaka, H.,Torii, S.
, p. 283 - 291 (2007/10/02)
Various bimetal redox systems Al/MXn (M=V, Nb, Co, Hg, Ge, Sn, Pb and Bi) were found efficient electron sources to promote the reductive coupling of benzaldehyde dimethylacetal into 1,2-diphenyl-1,2-dimethoxyethane 2a.Among these combinations the bimetal system Al/PbBr2 gives the best results with dimethylacetals derived from aromatic aldehydes leading to the corresponding 1,2-diaryl-1,2-dimethoxyethanes 2.On the other hand the reductive dimerization of acetals derived from aliphatic aldehydes does not take place with the previous bimetal redox systems Al/MXn, meanwhile under the same conditions the mixed acetals (α-methoxycarbamates) 4a,b lead to the corresponding carbamates 5a,b by hydrogenolysis of the carbon-oxygen bond (N-C-OMe).
