Studies in metal–ammonia reduction. Part 3. Reduction and reductive methylation of some acylnaphthalenes with metal–ammonia solutions

Abstract

Birch reduction and reductive methylation of 1- and 2-acetylnaphthalenes have been examined. It has been found that, while 1-acetylnaphthalene is reduced to the 3,4-dihydro-compound, the 2-acetylnaphthalene gives the corresponding 1,2,3,4-tetrahydro-compound. However, anhydrous ferric chloride has been found to limit the reduction and reductive methylation to the dihydro-stage with 2-acetylnaphthalene. The factors influencing the mechanism of the reduction process have been discussed. Some of the intermediate compounds are useful substrates in synthesis.