Sterically hindered aromatic compounds. XI. Spectral and product studies of the decomposition of N-nitrosoacetanilides

LRC Barclay, JM Dust

Index: Barclay, L. Ross C.; Dust, Julian M. Canadian Journal of Chemistry, 1982 , vol. 60, p. 607 - 615

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Citation Number: 6

Abstract

Decomposition of N-nitroso-2, 4, 6-tri-tert-butylacetanilide (1) in benzene forms products 2, 4, 6-tri-tert-butylphenyl acetate (3), 3-(3, 5-di-tert-butylphenyl)-2-acetoxy-2-methylpropane (4), and hydrocarbons 3-(3, 5-di-tert-butylphenyl)-and 1-(3, 5-di-tert-butylphenyl)-2- methylpropene (5 and 6) explained by a reactive aryl cation (2), the rearranged products (4, 5, 6) originating from a 1, 5-hydride shift from an ortho tert-butyl group in 2. In contrast, ...