The Synthesis of Novel Mono(alkoxy)-, Tris(thio)- and Tetrakis(thio)-Substituted Quinones from the Reactions of p-Chloranil with Various S-Nucleophiles

Abstract

The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7 and the mono(alkoxy)-tris(thio)-substituted-1,4- products 5a-e zinc 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alchol in the presence of Na(2)CO(3) at room temperature. The structures of the novel S,S,S,S- and S,S,S,O-substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.