A. Pozharskii, N. V. Vistorobskii, M. I. Rudnev
Aug 1, 1996
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0
Influential Citations
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Citations
Journal
Russian Chemical Bulletin
Abstract
Abstract4-Dimethy(amino-5-methoxynaphthylmethyl carbocation generated from 1-hydroxy methyl-4-dimethylamino-5-methoxynaphthalene in trifluoroacetic acid behaves as both diene and dienophile and undergoes (4π + 2π) cycloaddition to give an asymmetrical spiro compound. The other reaction product is 4,4'-bis(dimethylamino)-5,5'-dimethoxy 1,l'-dinaphthylmethane, which is formedvia ipso-substitution of the hydroxymethyl group in the initial alcohol. When this cation is generated on Al2O3, 4-dimethylamino-5-methoxy 1-naphthaldehyde is formed along with the substituted dinaphthylmethane.