Display Full Text | Download Full Text
1.07 MB PDF file

Degree

Master of Science (MS), Wright State University, Chemistry, 2011.

Abstract

Various 4-acyl-3-[2'-(carboalkoxy)phenyl]sydnones were synthesized by reaction of the parent sydnone with the corresponding anhydrides and Montmorillonite K-10. In the Q-tube, the acylation using acetic anhydride, which normally took 1.5 days for complete conversion thermally, was complete in 8.5 hours. Use of bismuth triflate as catalyst reduced the reaction time to 5 hours and, in the microwave, reactions were complete in 30 minutes and provided comparable yields. New sydnones were synthesized with acetic, propionic, butyric, and isobutyric anhydrides. Extension to various homogeneous metal triflates (lanthanum, yttrium, scandium, hafnium, gadolinium, and indium) was explored. Reactions were performed with 3-phenylsydnone as reactant, initially under thermal conditions overnight, individually with the six chosen catalysts. When optimal conditions were achieved, these predetermined parameters were employed for further optimization, performed under microwave irradiation. After multiple reactions, the best catalysts were determined to be the gadolinium and indium triflates.

Subject Headings

Chemistry

Keywords

sydnone; Friedel Craft acylation; metal triflate; microwave reaction

Committee / Advisors

Kenneth Turnbull, PhD (Advisor)
Eric Fossum, PhD (Committee Member)
Daniel Ketcha, PhD (Committee Member)

Pages

165p.

Document number: wright1316529382
Permalink: http://rave.ohiolink.edu/etdc/view?acc_num=wright1316529382

This ETD has been downloaded 197 times (through March 2013)