Date of Award
School of Social Work
Dr. Thomas W. Cole, Jr.
As part of an investigation of alternate routes to cu-bane derivatives and potentially physiologically active compounds related to cubane, 9,9-dimethoxy-l,2,3,4-tetrachloro-pentacyclo[4.3.j5q3,8g4,7]nonane was prepared. Attempts to hydrolyze this ketal with various concentrations of aqueous sulfuric acid were unsuccessful. Aqueous sulfuric acid (up to 75 percent) induced no reaction while concentrated sulfuric acid afforded an unsaturated ketone, isomeric with the desired cage tetrachloroketone. Spectral data support the assignment of this new ketone as 3,4,6,8-tetrachlorotricyclo[18.104.22.168z’ ]-nona-3,8-dien-7-one, arising via a carbonium ion rearrangement followed by a [1,3]-sigmatropic shift.
Norris, Herbert C., "A study of fifteen attempted suicides at the New York State training school for boys" (1949). ETD Collection for AUC Robert W. Woodruff Library. 3859.