Abstract
We report a novel fragmentation and functionalization method using a cyclic iminyl radical. Formation of this radical occurs by microwave heating under mild conditions and short reaction times. The reaction avoids the use of explosive or toxic radical initiators and propagating agents. This reaction is versatile, with the ability to install two functional groups that are ultimately derived from a ketone in the substrate precursor. A variety of radical traps capable of forming both carbon-carbon bonds and carbon-heteroatom bonds have been tested, and the products are obtained in good yields. We demonstrate the power of this reaction by functionalizing complex natural products.
Degree
MS
College and Department
Physical and Mathematical Sciences; Chemistry and Biochemistry
Rights
http://lib.byu.edu/about/copyright/
BYU ScholarsArchive Citation
Jackman, Mary Megan, "Microwave-Promoted Iminyl Radical Fragmentations: A Practical and Efficient Method of Functionalization" (2017). Theses and Dissertations. 6946.
https://scholarsarchive.byu.edu/etd/6946
Date Submitted
2017-08-01
Document Type
Thesis
Handle
http://hdl.lib.byu.edu/1877/etd9522
Keywords
methodology, iminyl radical, fragmentation, microwave irradiation
Language
english