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

Subba Rao, G. S. R. ; Shyama Sundar, N. (1982) Studies in metal-ammonia reduction. Part 3. Reduction and reductive methylation of some acylnaphthalenes with metal-ammonia solutions Journal of the Chemical Society, Perkin Transactions 1 . pp. 875-880. ISSN 1472-7781

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Official URL: http://pubs.rsc.org/en/content/articlelanding/1982...

Related URL: http://dx.doi.org/10.1039/P19820000875

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.

Item Type:Article
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