Benzylic sulfuric acid esters react with diverse functional groups and often form secondary reactive species

The mutagenicity of some benzylic sulfuric acid esters to Salmonella typhimurium is strongly influenced by monovalent anions and other medium components. The formation of highly mutagenic 1-chloromethylpyrene has been previously demonstrated. In the present study we found that the sulfuric acid esters of a primary benzylic alcohol, 1-sulfooxymethylpyrene, and a secondary benzylic alcohol, 4H-sulfooxycyclopenta[def]phenanthrene, exhibit reactivity towards many functional groups abundant in vivo. We identified various reaction products and determined their rates of formation. Many reaction products were still reactive. Their reactivity and selectivity towards nucleophiles varied over a wide range and was different from those of the parent sulfuric acid esters. Thus the formation of these secondary reactive species may explain many of the observed influences of medium components on the mutagenicity of benzylic sulfuric acid esters in vitro and may also affect their effects in vivo.