Synlett 2012; 23(13): 1893-1896
DOI: 10.1055/s-0032-1316557
letter
© Georg Thieme Verlag Stuttgart · New York

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

Ardeshir Khazaeia, Masoud Kazem-Rostami*a, Ahmad Reza Moosavi-Zarea, Mohammad Bayatb, Shahnaz Saedniaa
  • aDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 65178-38683 Hamedan, Iran, Fax: +98(811)8257407   Email: Masoud.kr@gmail.com
  • bDepartment of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran
Further Information

Publication History

Received: 07 May 2012

Accepted: 24 May 2012

Publication Date:
23 July 2012 (eFirst)

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.

 
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