Doctoral Dissertations
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.
Recommended Citation
Pippin, Adam Barret, "Boron and Metal Catalyzed C-C and C-H Bond Formation. " PhD diss., University of Tennessee, 2012.
https://trace.tennessee.edu/utk_graddiss/1553