Abstract: The synthesis of bicyclo [2.1. O] pentane-, bicyclo [3.1. O] hexane-, bicyclo [4.1. O] heptane-, bicyclo [5.1. O] octane-, and bicyclo [6.1. O] nonane-2, 3-semidiones has been investigated. Acyloin condensations of cis-l, 2-cyclopropanedicarboxylic esters failed to yield bicyclopentane semidiones. Instead, the ring-opened cyclopentanesemidiones were formed. Acyloin condensation or oxidation of the 2-or 3-ketones in basic solution ...