78312-49-9Relevant articles and documents
The Nitration of Thebaine with Tetranitromethane
Allen, Robert M.,Kirby, Gordon W.,McDougall, David J.
, p. 1143 - 1147 (1981)
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.