Substituent effects on the reactivity of benzo-1,2-dithiolan-3-one 1-oxides and their possible application to the synthesis of DNA-targeting drugs |
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Authors: | Sawwan Nahed Brzostowska Edyta M Greer Alexander |
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Institution: | Department of Chemistry, Graduate Center & The City University of New York (CUNY), Brooklyn College, Brooklyn, NY 11210, USA. agreer@brooklyn.cuny.edu |
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Abstract: | The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3-one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products. |
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