Design and development of novel reactions utilizing dienes and carbene intermediates

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Saad Sohail (Creator)
Institution
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/
Advisor
Mitchell Croatt

Abstract: The design and development of novel reactions are long-standing goals within the synthetic community. Specifically, reactions that can give molecularly complex products through the manipulation of readily available starting materials are of considerable interest. In pursuit of this goal, phenyl hypervalent iodonium alkynyl triflate (PhHIAT) is used as a precursor for the in situ generation of a reactive cyanocarbene intermediate. The reactive cyanocarbene was investigated as a potential gateway for synthesizing molecules of greater complexity. Specifically, novel reactions between cyanocarbenes and various symmetrical and unsymmetrical dienes were explored as a method for performing [2+1] cycloadditions. Preliminary reactions performed using a simple diene substrate showed promising results and further reactions allowed for the construction of an optimized procedure which was used on a variety of diene substrates. These reactions were studied for their potential viability as a method for accessing complex molecular moieties and to elucidate their mechanisms. The discovery of novel reactions adds to the tools that are at the disposal of the synthetic community and thus investigation into various synthetic methodologies can prove to be invaluable in achieving previously inaccessible or complex products in the most efficient way.

Additional Information

Publication
Thesis
Language: English
Date: 2020
Keywords
Carbene Intermediates, Cyanocarbenes, Dienes, Vinylcyclopropanes
Subjects
Chemical reactions
Diolefins
Carbenes (Methylene compounds)

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