Date of Award
Summer 1997
Document Type
Thesis - Restricted
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
McKinney, Michael A.
Second Advisor
Wilkie, Charles A.
Third Advisor
Cremer, Sheldon E.
Abstract
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.
Recommended Citation
Budowle, Mary K., "A Mechanistic Study of the Thermal Rearrangement of Cyclopropyl Dicarbonyl Compounds to Dihydrofurans" (1997). Master's Theses (1922-2009) Access restricted to Marquette Campus. 2438.
https://epublications.marquette.edu/theses/2438