REDUCTIVE FRAGMENTATION .3. SOLVATION EFFECTS IN REDUCTION OF BICYCLD(2.2.2)OCTYL TOSYLATES WITH LITHIUM ALUMINUM HYDRIDE

The reduction of 1-methyl-4-tosyloxy-bicyclo[2.2.2]octan-2-one (2) with LAH proceeds by fragmentation to 1-methyl-4-hydroxymethyl-4-methylene-cyclohexane (4) without any influence of the solvent on the product composition. On the other hand the course for the reduction of 1-methy-4-tosyloxy-bicyclol 2.2.2|octanon-2-ethylene acetal (12) depends on the nature of the solvent. Suspensions of LAH in diethyl ether give fragmentation reactions, homogeneous solutions in tetrahydrofurane lead to a cleavage of the OS bond with the result that the original alcohol 11 is reformed. The results are referred to solvation effects on the reducing agent. © 1969.