This invention relates to a novel class of 8-substituted bicyclo[3,2,1]octanes and to their preparation. More particularly, this invention is directed to novel 1,5-dimethyl-bicyclo[3,2,1]octane derivatives, substituted in the 8-position with halogen or cyanide substituents and to processes for their preparation starting with 1,5-dimethyl-1,5-cyclooctadiene or 1,5-dimethyl-bicyclo[3,2,1]octan-8-ol.
Certain 8-substituted 1,5-dimethyl-bicyclo[3,2,1]octane derivatives are known. For example, an article by J. K. Whitesell et al in Tetrahedron Letters No. 19 pp. 1549-1552 (1976) describes 8-hydroxy- and 8-tosyl-1,5-dimethylbicyclo[3,2,1]octane and their preparation from 1,5-dimethyl-1,5-cyclooctadiene. In this reference teaching, the 8-hydroxy-derivative is prepared by reacting the substituted cyclooctadiene with perchloric acid in a water-dioxane solution and the 8-hydroxy compound is subsequently converted to the tosylate by reaction with tosyl chloride in pyridine. Further, carboxylic acid esters of 1,5-dimethylbicyclo[3,2,1]octan-8-ol are described in copending U.S. Patent Application Ser. No. 37,196, filed May 8, 1979 (common assignee) as having distinctive aroma properties and utility as synthetic perfume materials. An attractive synthetic technique to preparation are these ester derivatives by hydrolysis or alcoholysis of 1,5-dimethyl-1,5-cyclooctadiene is disclosed in a second copending U.S. patent application (U.S. Ser. No. 37,195, filed May 8, 1979--common assignee).