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Preparation, reactivity and tautomeric preferences of novel (1H-quinolin-2-ylidene)propan-2-ones

Lookup NU author(s): Dr Hosein Loghmani-Khouzani, Dr Ross Harrington, Emeritus Professor Bill CleggORCiD


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1,1-Difluoro-3-(1H-quinolin-2-ylidene)propan-2-one 1a, 1,1,1-trifluoro-3- (1H-quinolin-2-ylidene)propan-2-one 1b, 1,1,1-trifluoro-3-(4-chloro-1H-quinolin- 2-ylidene)propan-2-one 1c and 1,3-dibromo-1,1-difluoro-3-(2-quinolyl)propan-2- one 2 are prepared and characterized by various spectroscopic techniques. The crystal structure of la is determined by X-ray diffraction. Furthermore, a series of previously known non-halogenated (1H-quinolin-2-ylidene)propan-2-ones 1d-1h are oxidized with AgBrO3 in the presence of AlCl3. In all cases, 2-(1-bromo-1-chloromethyl)quinoline 3 is obtained in high yield. The bromination order and sites of la are analyzed based on ab initio MP2 and DFT calculations for the molecule and its anions.

Publication metadata

Author(s): Loghmani-Khouzani H, Osmailowski B, Gawinecki R, Kolehmainen E, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Journal of the Iranian Chemical Society

Year: 2006

Volume: 3

Issue: 2

Pages: 173-179

ISSN (print): 1735-207X

ISSN (electronic): 1735-2428

Publisher: Iranian Chemical Society