Issue 0, 1981

The nitration of thebaine with tetranitromethane

Abstract

Thebaine (1) reacts in methanol with tetranitromethane to give, as the major product, 14β-nitrocodeinone dimethyl acetal (2a), which has been converted into, inter alia, 14β-nitrocodeinone (3a), 14β-aminocodeinone dimethyl acetal (2b), 14β-aminocodeinone (3b), and 14β-aminocodeine. The nitration of thebaine with tetranitromethane in benzene in the presence of oxygen takes a different course. The major product has been identified as the cyclic peroxide 8α,10α-epidioxy-8,14-dihydro-14β-nitrothebaine (5) by a series of degradations leading to new 10α-hydroxy- and 10-oxo-thebaine derivatives.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1143-1147

The nitration of thebaine with tetranitromethane

R. M. Allen, G. W. Kirby and D. J. McDougall, J. Chem. Soc., Perkin Trans. 1, 1981, 1143 DOI: 10.1039/P19810001143

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