Metal-ammonia ring reduction of aromatic carboxylic acid esters

PW Rabideau, DM Wetzel…

Index: Rabideau, Peter W.; Wetzel, Donna M.; Young, Michael D. Journal of Organic Chemistry, 1984 , vol. 49, p. 1544 - 1549

Full Text: HTML

Citation Number: 19

Abstract

Although esters are often reduced to alcohols with metal-ammonia solutions, it has been found that aromatic carboxylic acid esters can be reduced efficiently to the corresponding dihydro aromatics when 1.25 equiv of water is present before metal addition. The general effect of the presence of water (before metal addition) upon metal-ammonia reduction of polycyclics was tested with anthracene (0.5 g), which was reduced to 9, lO- ...