Resonance-stabilized ?-naphthylmethyl carbocations and derived spiro compounds 4. T-ansformations of 4-dimethylamino-5-methoxynaphthylmethyl carbocation in the presence of protic and Lewis acids. The formation of an asymmetrical spiro compound
作者:A. F. Pozharskii、N. V. Vistorobskii、M. I. Rudnev、A. I. Chernyshev
DOI:10.1007/bf01457780
日期:1996.8
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
摘要 1-羟基甲基-4-二甲氨基-5-甲氧基萘在三氟乙酸中生成的4-二甲基(氨基-5-甲氧基萘甲基碳正离子)既是二烯又是亲二烯体,经过(4π+2π)环加成生成不对称螺环化合物。反应产物是 4,4'-双(二甲氨基)-5,5'-二甲氧基 1,1'-二萘甲烷,它是通过初始醇中的羟甲基同位取代形成的。当这种阳离子在 Al2O3 上生成时,4 -二甲氨基-5-甲氧基1-萘醛与取代的二萘甲烷一起形成。