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.
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.
Sawwan
Nahed
N
Department of Chemistry, Graduate Center & The City University of New York (CUNY), Brooklyn College, Brooklyn, NY 11210, USA. agreer@brooklyn.cuny.edu
Brzostowska
Edyta M
EM
Greer
Alexander
A
D004247:DNA / Q000187:drug effects*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010087:Oxides / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry
D010087:Oxides; D014050:Toluene; D004247:DNA; C004848:dithiol