Substituent Effects on the Reactivity of Benzo-l,2-dithiolan-3-one 1-Oxides and Their Possible Application to the Synthesis of DNA-Targeting Drugs

摘要

The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-l,2-dithiolan-3-one 1-oxides in ac-etonitrile-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.