Date of Award

12-2012

Degree Type

Dissertation

Degree Name

Doctor of Philosophy

Major

Chemistry

Major Professor

George W. Kabalka

Committee Members

John E. Bartmess, David M. Jenkins, Kimberly D. Gwinn

Abstract

Research efforts focused on the use of boron and metals to form new carbon-carbon and carbon-hydrogen bonds are summarized in this dissertation. Several novel reactions have been developed. These include: the deoxygenation of benzylic alcohols using chloroboranes; alkenylation of benzylic alcohols using boron trichloride; and dialkynlation of aryl aldehydes using dialkynylboron chloride. Numerous applications of these novel reactions have been developed. These include alternate routes to diphenylmethanes and 1,4-diynes from easily prepared dialkynylboron chlorides. In addition, E and Z alkenyl halides can now be prepared using boron trichloride without the use of butyllithium. The stereochemistry of the alkenyl halide can be altered using various reaction conditions. This type of methodology and previously reported indium allylation chemistry was applied to the synthesis of naturally occurring lactones.

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