Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions

This paper is dedicated to Professor Rudolf Leuckart for his studies on mercaptans.

Abstract

In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines.

Key words

thiophenol - aryl amine - triazene - diazonium salt - one-pot synthesis

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