Journal of Organic Chemistry p. 1182 - 1185 (1984)
Update date:2022-08-05
Topics:
Majerski, Zdenko
Hamersak, Zdenko
4,5-exo-Epoxybrendane (3) rearranged readily with sulfuric acid in acetone, and with boron trifluoride etherate in acetic acid, yielding, upon a hydrolytic workup, 86percent of 2-exo-8-exo-noradamantanediol and 93percent of 8-exo-acetoxy-2-exo-noradamantanol, respectively.Starting epoxide 3 was prepared in 60percent overall yield from readily available 4-brendanone.Consequently, the acid solvolysis of 3 provides a convenient, general entry to the noradamantane system functionalized at carbons 2 and 8.
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