The 20th annual Symposium will be held on Thursday, April 23, 2009.

Synthesis and PET Reactions of o-alkyl Oximes
Norris 100, 3:30 PM

Matthew  Logan,   '10 18
   Major: Chemistry
   Hometown: Brooklyn, MI

Sponsor(s): Andrew French
Support: National Science Foundation Research Experience for Undergraduates at the California State University, Fullerton

Abstract: 
The synthesis of O-alkyl oximes with built-in hydroxy nucleophiles has been successfully developed from benzaldehyde and allyl magnesium bromide. Hydroboration-oxidation of the resulting alkene followed by selective oxidation of the benzylic hydroxyl group yielded the desired hydroxy ketone, however oximation of this substrate was not successful. Instead it was found that protection of the hydroxy group was required. The hydroxyl group which was successfully protected as a tert-butyldimethyl silyl ether and oximation of the ketone, followed by deprotection of the silylated hydroxyl group successfully yielded the desired O-methyl oxime with the built-in aliphatic hydroxyl. The multi-functionalized O-methyl oxime substrate was then subjected to photoinduced electron transfer (PET) reactions to yield several products, which have not yet been identified. The synthesis of these molecules is critical to understanding the behavior and reactivity of O-alkyl oximes radicals in the presence of nucleophilic solvents. The developed methodology will allow for a broad array of O-alkyl oximes with built-in nucleophiles to be studied.

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