Journal of the Chemical Society. Perkin transactions I p. 1143 - 1147 (1981)
Update date:2022-08-02
Topics:
Allen, Robert M.
Kirby, Gordon W.
McDougall, David J.
Thebaine (1) reacts in methanol with tetranitromethane to give, as 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.
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