Studies in the Tricyclooctane Series. I. Dehydrohalogenation of Some Bis-halogenocarbene Adducts of Cyclohexadienes

Abstract

Reaction between 4,4,8,8-tetrachloro-cis-transoid-cis-tricyclo[5,1,0,0^3,5]octane (1d) and potassium t-butoxide leads to the (E)- and (Z)-β-t-butoxy-4-chlorostyrenes (8a,b). The epimeric 4,4,8-trichloro analogues (1e,f) behave similarly to give (E)-β-t-butoxystyrene (8c) as the sole isolable product in low yield. Under the same conditions the corresponding tri- and tetra-chloro-cis-transoid-cis-tricyclo[5,1,0,0^2,4]octanes (7d-f) yield complex product mixtures. Evidence is presented which suggests the non-involvement of halogenocyclooctatetraenes in these reactions.