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

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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Veröffentlicht in:	Journal of organic chemistry 2006-01, Vol.71 (2), p.789-791
Hauptverfasser:	Sheldrake, Gary N, Soissons, Nicolas
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Models, Molecular Molecular Conformation Morphine - chemistry Nitroso Compounds - chemistry Organic chemistry Preparations and properties Thebaine - chemistry
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Beschreibung
Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo052016j