Physical Sciences and Mathematics Commons^™

New Chemistry Of Donor-Acceptor Cycloalkanes And Studies Towards The Synthesis Of Streptorubin B, Naresh Vemula

Electronic Thesis and Dissertation Repository

This dissertation presents two separate chapters within the broad area of synthetic organic chemistry. The first chapter describes the annelation chemistry of donor-acceptor (DA) cyclopropanes and cyclobutanes for the synthesis of heterocycles. The Yb(OTf)₃-catalyzed [4+2] cycloaddition between DA cyclobutanes and nitrosoarenes facilitated the synthesis of tetrahydro-1,2-oxazines in good to excellent yields as single diastereomers. Additionally, an unexpected deoxygenation occurred with electron-rich nitrosoarenes under MgI₂-catalysis that afforded pyrrolidine products. The GaCl₃-catalyzed [4+2] cycloaddition of DA cyclobutanes and cis-diazenes provided hexahydropyridazine derivatives in good to excellent yields as single diastereomers. Furthermore, a procedure to make …

Synthesis And Electrochemiluminescence Of Thiophene Substituted Benzosiloles, Tyler J. B. Day

Electronic Thesis and Dissertation Repository

There has been increasing interest in the synthesis of siloles over the past 20 years due to their applications as chemoselective sensors and light emitting diodes. The standard synthesis of siloles involves a one-pot reductive cyclization followed by Negishi cross-coupling, which was modified by the Pagenkopf group to allow the synthesis of dissymmetric siloles. This modified synthesis allows siloles to be tuned to improve their fluorescent properties via varying substituents on the silole. This culminated in the synthesis of a series of 2,5-bis(thiophene)siloles with bulky silyl substituents that displayed excellent electrochemiluminescent properties.

In the past decade there has been a …