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Heterocyclic o-Chloroaldehydes as Synthons in Organic and Inorganic Sulfur Chemistry
Authors:Jan Becher
Institution:Department of Chemistry , Odense University , DK-5230, Odense M, Denmark
Abstract:Abstract

Many heterocyclic o-chloroaldehydes are easy to prepare, for example via the Vilsmeier chloroformylation reaction. Due to the electron withdrawing effect of the formyl group, the halogen atom is normally a nucleofuge. This can be used to prepare a range of o-substituted heterocyclic aldehydes showing interesting rearrangement reactions. Such types of compounds are also useful as starting materials for the preparation of annelated heterocyclic systems.

We have demonstrated that heterocyclic mercapto groups can be protected as t-butylthioethers. Furthermore, we have found that thiolation of heterocyclic systems containing reactive halogen substituents can conveniently be carried out via the easily prepared t-butylsulfides.

This method has been used in the preparation of a number of N2S2-ligands. The resulting transition metal N2S2-complexes have been used in the study of model systems for one of the active sites in cytochrome c oxidase. The method also gives access to polymeric heterocyclic multisulfur transition metal complexes with high electrical conductivity.
Keywords:Thianthrene diquinones  cyclovoltammograms  radical ion pair  triple ion radical cation  ESR/ENDOR  
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