Universität Rostock, 2009
Abstract: The work presented in this dissertation is concerned with the regioselective synthesis of functionalizeddiarylsulfides. The first chapter includes the synthesis of functionalized 2-(phenylthio)benzoates, containing a halogenated side chain, by domino ‘[3+3] cyclization / Homo-Michael′ reactions of 1-trimethylsilyloxy-3-arylthio-1,3-butadienes with 1,1-diacylcyclopropanes. In the second chapter, a regioselective synthesis of 2-(arylthio)benzoates by the first [3+3] cyclizations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-alkoxy-2-en-1-ones is reported. In the third chapter, the synthesis of 5-arylthio-3-hydroxyphthalates by the first [4+2] cycloadditions of 3-arylthio-1-silyloxy-1,3-butadienes with dimethyl acetylenedicarboxylate is reported.
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