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Regioselectivity in Free Radical Bromination of Unsymmetrical Dimethylated Pyridines

Thapa, Rajesh
http://rave.ohiolink.edu/etdc/view?acc_num=miami1263340046

Abstract Details

2010, Master of Science, Miami University, Chemistry and Biochemistry.
During a literature review some curious inconsistencies in the free radical bromination of picolines were noted. To achieve a better understanding of the mechanisms and regioselectivity we reran these reactions, extending our work to unsymmetrical lutidines using N-bromosuccinimide in limiting amount. Characterization of the products was done with GC/MS and H NMR. The regioselectivity of bromination in unsymmetrical dimethylpyridines shows that nitrogen in the ring is deactivating inductively. The competition between 2,3, 2,4 and 2,5 dimethyl pyridine towards bromination results with bromination in the methyl group farthest from the N in the ring. 3,4-Lutidine shows only the 4,4- dibrominated product.
Dr. Gilbert Ellery Pacey, PhD (Committee Chair)
Dr. Richard T. Taylor, PhD (Advisor)
Dr. Benjamin W. Gung, PhD (Committee Member)
Dr. Hong Wang, PhD (Committee Member)
69 p.
Chemistry
NBS; RADICAL BROMINATION; FREE RADICAL; bromine; FREE RADICAL BROMINATION

Recommended Citations

Citations

  • Thapa, R. (2010). Regioselectivity in Free Radical Bromination of Unsymmetrical Dimethylated Pyridines [Master's thesis, Miami University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=miami1263340046

    APA Style (7th edition)

  • Thapa, Rajesh. Regioselectivity in Free Radical Bromination of Unsymmetrical Dimethylated Pyridines. 2010. Miami University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=miami1263340046.

    MLA Style (8th edition)

  • Thapa, Rajesh. "Regioselectivity in Free Radical Bromination of Unsymmetrical Dimethylated Pyridines." Master's thesis, Miami University, 2010. http://rave.ohiolink.edu/etdc/view?acc_num=miami1263340046

    Chicago Manual of Style (17th edition)

miami1263340046
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© 2010, all rights reserved.
This open access ETD is published by Miami University and OhioLINK.