Physical Sciences and Mathematics Commons^™

The Theory And Synthesis Of [2.2.2] Propellane, Theodore Mark Prociv

Dissertations, Theses, and Capstone Projects

INDO calculations indicated that the triplet state of dimethylene cyclohexane could rearrange to gometrically relaxed triplets which should collapse preferentially to the ground state [2.2.2] Propellane. A mercury sensitized photolysis of the dimethylene cyclohexane did in fact result in detectable quantities of the propellane, trapped as 1,4 dibromobicyclo octane. Synthesis of 1,4 dibromobicyclo octane and 1,1,6,6 tetradeuterodimethylene-cyclohexane are presented in the dissertation. Included in the dissertation are the results of INDO calculations of various propellane isomers having nitrogens and borons in the bridgehead positions.