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Note | Regular issue | Vol 57, No. 1, 2002, pp.135-142
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9378
Formation of a New Polycyclic Heteroring System by the Acid-catalyzed Rearrangement of Thebaine in the Presence of Thiosalicylic Acid

Sándor Berényi,* Miklós Tóth, Susanna Gyulai, and László Szilágyi

*Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O.Box 20, Hungary


The methanesulfonic acid-catalyzed rearrangement of thebaine (1) in the presence of thiophenol resulted in 2-phenylthioapocodeine (7), whose O-demethylation gave 2-phenylthioapomorphine (8). An analogous transformation of 1 with thiosalicylic acid furnished the ethers (6) and (11) together with a polycyclic ketone (12) and a polycyclic acetal (15). Upon treatment of the acetal (15) with acid the thioxanthylium salt (16) was prepared.