Date of Award

Summer 1997

Document Type

Thesis - Restricted

Degree Name

Master of Science (MS)



First Advisor

McKinney, Michael A.

Second Advisor

Wilkie, Charles A.

Third Advisor

Cremer, Sheldon E.


The thermal rearrangement of cycopropyl dicarbonyl compounds to dihydrofurans has not been as thoroughly studied as the similar rearrangement of vinyl cyclopropanes to cyclopentenes. Several different mechanisms are possible in the thermal rearrangement of 6,6-dimethyl- l-phenylspiro-[2,5]-octan-dione (8) to 6,6-dimethyl-2,3,6,7- tetrahydro-5H-I-oxainden-4-one (9). The solvent effect, substituent effect, stereochemistry, and activation parameters of this reaction were studied in the attempt to uncover the mechanism of the reaction. The study of the thermal rearrangement of E and Z-6,6-dimethyl-2-phenyl-5 -oxaspiro-[2,5]-octan-4,8-dione (10) to 6,6-dimethyl-2-phenyl- 2,3,6,7-tetrahydro-7H-1-dioxainden-4-one (11) was selected to further study the overall mechanism.



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