Clemmensen Reduction. IX. Structure and Reactions of a Cyclopropane-1,2-diol

Abstract

The β-keto aldehyde , 1-methyl-2-oxocyclododecanecarbaldehyde (4), was converted into a mixture of two cyclopropane-1,2-diyl diacetates , 12- methyl- cis-bicyclo [10.1.0]tridecane-cis-1,13-diyl diacetate (6) and 12- methyl-trans- bicyclo [10.1.0]tridecane-trans-1,13-diyl diacetate (8). The structure of (6) was established by means of a single-crystal X-ray study. The crystals are monoclinic, space group P2₁/c, with four molecules in a unit cell of dimensions a 12.326(1), b 14.998(2), c 10.388(3) Ǻ, β 108.33(1)°. The structure was solved by direct methods, and refined to an R factor of 0.059. Protonolysis of the corresponding diols leads to compounds not normally encountered in such systems but the genesis of the major products can be rationalized.