Triyclo3,7>decan (9-Homo-nor-adamantan) Synthese und Umwandlungen

Article abstract of DOI:10.1002/hlca.19800630735

A synthesis of tricyclo<3.3.2.0^3,7>decane (= 9-homo-nor-adamantane; 1), which belongs to the adamantaneland, a family of nineteen isomeric C10H16 hydrocarbons, is described, as well as derivatives thereof.Treatment of protoadamantan-5endo-ol (11) with either thionyl chloride or phosphorus pentachloride yielded under rearrangement the chloride 18, and solvolysis of the 5endo-chloroprotoadamantane (16) led to the acetate 26, 18 and 26 having both the tricyclo<3.3.2.0^3,7>decane skeleton.Subsequent transformations gave the title compound 1 as well as the corresponding olefin 8.