Rearrangements of 1,6-Dihalotricyclo2,5>decanes. Synthesis of Tricyclo4,8>decane Derivatives

Article abstract of DOI:10.1021/jo01292a024

1,8-Diiodotricyclo<5.3.0.0^4,8>decane (16) was prepared by reaction of 1,6-dihalotricyclo<4.2.2.0^2,5>decanes 9a and 9b with aluminum triiodide.Reduction of 16 with n-butyltin dihydride produced the tricyclic hydrocarbon tricyclo<5.3.0.0^4,8>decane (1).Dichloride 9a was prepared by a Diels-Alder reaction between 1,4-dichlorocyclohexa-1,3-diene (10a) and cyclobutene followed by catalytic hydrogenation of the adduct 12a.The structure of 16 was determined by an X-ray diffraction study of a single crystal.