88685-74-9Relevant academic research and scientific papers
Synthesis and Chemistry of 2,8-Disubstituted Noradamantanes
Majerski, Zdenko,Hamersak, Zdenko
, p. 1182 - 1185 (1984)
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.
