Type of Document	Thesis
Author	Brookover, Kimberly Ann
Author's Email Address	brookovr@chem.fsu.edu
URN	etd-07072005-165319
Title	The Morita-Baylis-Hillman Cycloalkylation Reaction
Degree	Master of Science
Department	Chemistry and Biochemistry, Department of
Advisory Committee	Advisor Name Title Greg Dudley Committee Member Kenneth Goldsby Committee Member Marie E. Krafft Committee Member Robert A. Holton Committee Member
Keywords	Cyclization Reaction Morita-Baylis-Hillman Organomediated Alky Halide Alkylation Phosphine Catalyst
Date of Defense	2005-07-01
Availability	unrestricted
Abstract The Morita-Baylis-Hillman reaction dates back to German and Japanese patents where both Morita, and Baylis and Hillman, discovered a new carbon-carbon bond forming reaction involving a nucleophilic catalyst, an activated alkene, and an electrophile. Although this reaction was discovered in the early 1970’s, it was not until over a decade later that researchers took notice and began to thoroughly investigate this reaction. Since then, this reaction has seen tremendous growth in all three components, however the application of simple unactivated alkyl halides as the electrophilic partner has never been reported. Herein, a new version of the Morita-Baylis-Hillman reaction has been discovered that uses unactivated sp3 hybridized halides as the electrophilic partner. It has also been shown that this reaction tolerates alterations on the tether as well as the increase of steric bulk on the enone moiety. This reaction is a convenient and simple route for the synthesis of five- and six-memebered ring compounds in extremely high yields.
Files	Filename       Size       Approximate Download Time (Hours:Minutes:Seconds)     28.8 Modem   56K Modem   ISDN (64 Kb)   ISDN (128 Kb)   Higher-speed Access    BrookoverKThesis.pdf 4.01 Mb 00:18:33 00:09:32 00:08:20 00:04:10 00:00:21