Abstract
THE very various transformations undergone by 9-acetyl-10 : 11-dihydroxyhexahydrocarbazole (I) have recently aroused some interest1. The related compound (II) does not undergo Wagner–Meerwein rearrangements like those given by (I)2. Witkop1a has satisfactorily explained this failure by pointing out that such rearrangement of (II) would involve the formation of a four-membered ring compound. While this suggestion is convincing, it seemed worth while to confirm that the diols (I) and (II) possess similar configurations, for the Wagner–Meerwein change is markedly affected by the cis- or trans-configuration of the compound involved, only the cis-diols becoming readily rearranged3. Further, (I) and (II) have hitherto been prepared by rather different methods.
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References
(a) Witkop, J. Amer. Chem. Soc., 72, 614 (1950). (b) Patrick and Witkop, ibid., p. 633. (c) Witkop and Patrick, Experientia, 6, 183 (1950) and later publications. (d) Plant and Robinson, Nature, 165, 36 (1950). (e) Plant and Tomlinson, J. Chem. Soc., 2127 (1950).
Plant and Tomlinson, J. Chem. Soc., 298 (1933).
Wheland, “Advanced Organic Chemistry”, 519 (2nd edit., New York, 1949).
This work is summarized by Schofield, Quart. Rev. Chem. Soc., 4, 391 (1950).
Plant and Whitaker, J. Chem. Soc., 283 (1940).
Criegee, Annalen, 522, 75 (1936).
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OCKENDEN, D., SCHOFIELD, K. Perhydroxylation of Indole Derivatives by Osmium Tetroxide. Nature 168, 603 (1951). https://doi.org/10.1038/168603a0
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DOI: https://doi.org/10.1038/168603a0
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