MORPHINE ALKALOIDS .121. REARRANGEMENT OF MORPHINANDIENES IN METHANESULFONIC-ACID

Authors
BERENYI S CZIRJAK M MAKLEIT S
Citation
S. Berenyi et al., MORPHINE ALKALOIDS .121. REARRANGEMENT OF MORPHINANDIENES IN METHANESULFONIC-ACID, Journal of the Chemical Society. Perkin transactions. I, (17), 1993, pp. 2137-2139
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
17
Year of publication
1993
Pages
2137 - 2139
Database
ISI
SICI code
0300-922X(1993):17<2137:MA.ROM>2.0.ZU;2-6
Abstract
Besides 2-fluoroapocodeine 7, the methanesulfonic acid-induced rearran gement of 6-fluoro-6-demethoxythebaine 2 gave the C-2 substituted apoc odeines 8, 11 and 20. Analogous rearrangement of thebaine 1 in the pre sence of alcohols offers a convenient and high-yielding route to the 2 -alkoxymorphothebaine 6, 11, 12 and 13. Formation of the products has been explained in terms of nucleophilic substitution of the cationic i ntermediates 21 and 22 from the acid-catalysed reaction.