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Chemistry Faculty Publications

Fordham University

3,5-Dibromo-4,8-quinolindiol

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Effect Of Dimethyl Sulfoxide And Dimethylformamide On The Stability Of 4-Halo-8quinolinols / Herman Gershon, Donald D. Clarke, And John J. Mcmahon Department Of Chemistry, Fordham University, Bronx, Ny 10458-9993, Usa New York Botanical Garden, Bronx, Ny 10458-9993, Usa, Herman Gershon, Donald Dudley Clarke Phd, John J. Mcmahon Jan 2003

Effect Of Dimethyl Sulfoxide And Dimethylformamide On The Stability Of 4-Halo-8quinolinols / Herman Gershon, Donald D. Clarke, And John J. Mcmahon Department Of Chemistry, Fordham University, Bronx, Ny 10458-9993, Usa New York Botanical Garden, Bronx, Ny 10458-9993, Usa, Herman Gershon, Donald Dudley Clarke Phd, John J. Mcmahon

Chemistry Faculty Publications

Polyhalo-8-quinolinols with chlorine or bromine in position 4 were not stable in DMSO or DMF. The degradation product from 4,5-dichloro-8-quinolinol was 5-chloro-4,8-quinolindiol and the major product from 4,5-dibromo-8-quinolinol was 3,5-dibromo-4,8-quinolindiol. 4,5,7-Trichloro- and 4,5,7-tribromo-8-quinolinols yielded similar hydrolytic products, and for the bromo compound, a rebrominated product in DMSO. In DMF rebrornination did not occur. In pyridine-d5 these reactions did not take place, indicating a special ability of DMSO and DMF to cause such hydrolysis at position 4 of 4-halo-8-quinolinols