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2004
Bridged compounds
Q 0060
Transformations of 2-(3-Hydroxy-3-methyl-1-butynyl)adamantan-2-ol Catalyzed
Acids. — The reaction of title diol (I) with MeCN under Ritter reaction conditions
51- 064 by
proceeds with isomerization and partial hydration to afford a mixture of amino ketones
(IV) and (V) and diamine (III). Interestingly, the addition of water proceeds without
any regioselectivity. Rupe rearrangement of compound (I) affords a mixture of dihydroxy ketones (VII)/(VIII) instead of the expected α,β-unsaturated ketones. —
(KOVAL'SKAYA, S. S.; KOZLOV, N. G.; DIKUSAR, E. A.; Russ. J. Org. Chem. 40
(2004) 5, 668-674; Inst. Phys. Org. Chem., Natl. Acad. Sci. Belarus, Minsk 220072,
Belarus; Eng.) — Mischke
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