6. “The predictable behaviour of cations deriving from endo-4-chlorotetracyclo[3.3.0.0.^2,8O.^3,6]octane”
   C.W. Jefford, S. Genevay-Höck, A. Delay, J. Mareda, U. Burger
   Tetrahedron Lett. 1979, 20, 2549-2552.

Silver cation-initiated ionization of the title compound in aqueous dioxane gives theexo and endo-tetracyclo[3.3.0.0.^2,8O.^4,6]octane-3-ols (35 and 65%). Thermal isomerization in chloroform gives the exo and endo isomers of 4-chlorobicyclo[3.2.1]octa-2,6-dienes (3.5 and 1.5%) and 6-chlorotricyclo[3.2.1.0.^2,7]oct-3-ene (90 and 5%). The behaviour of the cations involved is compatible with MINDO/3 calculations.

DOI : 10.1016/S0040-4039(01)86345-0 

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