Date of Award

6-1-1949

Degree Type

Thesis

Degree Name

M.S.W.

Department

School of Social Work

First Advisor

Dr. Thomas W. Cole, Jr.

Abstract

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[4.3.0.0z’ ]-nona-3,8-dien-7-one, arising via a carbonium ion rearrangement followed by a [1,3]-sigmatropic shift.

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