Abstract
S-Oxides of dithiinodiquinolines (4) and (5) react with potassium phenoxide at γ-quinolinyl-sulfur bond in two manners. Sulfinyl moiety at non-aza-influenced position in sulfoxide (5) significantly activates orthosulfanyl substituent towards nucleophilic phenoxy-de-sulfidation to form quinolinethiolate (6A). In the case of sulfoxide (4) with sulfinyl group in aza-activated position, nucleophilic phenoxy-de-sulfinylation occurs to form quinolinesulfenate anion (7A) trapped finally by methylation to products (8), (9) and (10).
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