Publication Date


Document Type


Committee Members

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

Degree Name

Master of Science (MS)


An important research element in the Turnbull laboratory has been the one-pot synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one from sydnone. The present study reexamined the reaction of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one with electrophiles and optimized methods for synthesis of oxadiazolinone derivatives. Further the oxadiazolinone derivatives were reacted with electrophiles to better comprehend the donating ability of the oxadiazolinone ring system in general with the expectation that the oxadiazolinone ring system is a slightly donating system. Additionally, when the structure assignment of the oxadiazolinone derivative was ambiguous, the corresponding oxadiazolinone or it’s isomer was synthesized from the appropriate sydnone to validate or refute the suggested structure. The results of the present study showed the reproducibility of experiments done by previous interns in the Turnbull laboratory. The procedure for nitration of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one could be optimized. Extension of nitration to para substituted oxadiazolinones resulted in di-substituted derivatives. Through these nitration studies, the oxadiazolinone ring system is shown to be a moderate donor.

Page Count


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons