Selective opening of ring C in the morphine skeleton by an unexpected cleavage of the C5-C6 bond in cycloadducts of thebaine and acyl nitroso compounds.

Abstract

[reaction: see text] Acyl nitroso cycloadducts of the alkaloid thebaine undergo an unexpected cleavage of the C5-C6 bond when treated with 2 equiv of samarium(II) iodide in THF to give novel hexahydrobenzazocine products. A proposed mechanism for the transformation involves rearrangement of the initial radical anion. 

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Cite this paper

@article{Sheldrake2006SelectiveOO, title={Selective opening of ring C in the morphine skeleton by an unexpected cleavage of the C5-C6 bond in cycloadducts of thebaine and acyl nitroso compounds.}, author={Gary N Sheldrake and Nicolas Soissons}, journal={The Journal of organic chemistry}, year={2006}, volume={71 2}, pages={789-91} }