Issue 18, 1969
From the journal:

Journal of the Chemical Society C: Organic

Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part X. Further acid-catalysed rearrangements of alcohols in the 6,14-endo-ethenotetrahydrothebaine series

K. W. Bentley,   D. G. Hardy,   B. Meek,   J. B. Taylor,   J. J. Brown  and  G. O. Morton  

Abstract

Thebaine-derived alcohols of general structure (4), showing chain branching on the carbon atom adjacent to the alcoholic centre, can be rearranged in acids in a manner different from alcohols in which there is no such chain branching, to give initially derivatives of furano[2′,3′ :6,7] codide (8 and 9) and finally, by a process that can be represented as proceeding through a bridgehead carbonium ion, derivatives of cyclopenteno[3′,2′ :6,7]codide (13 and 14). The αβ-unsaturated carbinol (22) in contrast rearranges through the codeinone (24) and pyranocodide (25) to the thebainone-A derivative (26).

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Article information

DOI
https://doi.org/10.1039/J39690002229
Article type
Paper

J. Chem. Soc. C, 1969, 2229-2232

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Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part X. Further acid-catalysed rearrangements of alcohols in the 6,14-endo-ethenotetrahydrothebaine series

K. W. Bentley, D. G. Hardy, B. Meek, J. B. Taylor, J. J. Brown and G. O. Morton, J. Chem. Soc. C, 1969, 2229 DOI: 10.1039/J39690002229

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