Wednesday, 16 May 2007
3rd Floor Hall (Pfahler Hall)
57

Lewis acid - mediated ring expansion of azetidines to benzazepines

Maryll E. Geherty and Lynn M. Bradley. The College of New Jersey, Ewing, NJ

The major goal of this project is to synthesize the biologically active compound 2,3,4,5-Tetrahydro-1H-2-benzazepine from ortho-bromobenzylazetidine. This research focuses on the use of halogen-metal exchange chemistry in order to create a nucleophilic carbanion at the bromine-bound-carbon on the benzene ring. This carbanion in theory should open the azetidine ring, ultimately resulting in the formation of 2-benzazepine. Initial NMR and mass spectral data, as well as elemental analysis, indicate that with the use of a strong Lewis acid, the azetidine can be activated to undergo ring expansion to form the final benzazepine compound indicated below.


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