Synthesis and Reactions of Biradicals and o-Quinodimethanes

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9307994 Wang The focus of this research is the development of new methods for the synthesis of enediynes and enyne-allenes which provide easy entries to a variety of carbon diradicals and mechanistic studies of the subsequent radical processes. The first objective is to develop the use of the condensation reaction of sillylallenylboranes with acetylenic and allenic aldehydes for the synthesis of enediynes and enyne-allenes having diverse chemical structures. New synthetic routes to enediynes, enyne-allenes, diene-allenes, enediallenes and other related structures via the intramolecular migration reaction of organoborate complexes will also be developed. The formation of carbon diradicals from these unsaturated compounds will be studied using the strategy of generating new types of diradicals by intramolecularly capturing the initially formed diradical with a properly situated carbon-carbon double or triple bond. This will allow the radical centers to be moved around the molecule and can lead to the formation of other reactive species, such as o-quinodimethanes. %%% With this award, the Synthetic Organic Program is supporting the research of Dr. Kung K. Wang of the Department of Chemistry at West Virgina University. Professor Wang will focus his work on synthetic methods generating new types of carbon diradicals and the mechanistic studies of the subsequent radical processes which have recently found their counterpart in biological systems. ***