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

Ardeshir Khazaei; Masoud Kazem-Rostami; Ahmad Reza Moosavi-Zare; Mohammad Bayat; Shahnaz Saednia

doi:10.1055/s-0032-1316557

Synlett, Table of Contents

Synlett 2012; 23(13): 1893-1896
DOI: 10.1055/s-0032-1316557

letter

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

Ardeshir Khazaei

^aDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 65178-38683 Hamedan, Iran, Fax: +98(811)8257407 Email: Masoud.kr@gmail.com

,

Masoud Kazem-Rostami*

^aDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 65178-38683 Hamedan, Iran, Fax: +98(811)8257407 Email: Masoud.kr@gmail.com

,

Ahmad Reza Moosavi-Zare

^aDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 65178-38683 Hamedan, Iran, Fax: +98(811)8257407 Email: Masoud.kr@gmail.com

,

Mohammad Bayat

^bDepartment of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran

,

Shahnaz Saednia

^aDepartment of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, 65178-38683 Hamedan, Iran, Fax: +98(811)8257407 Email: Masoud.kr@gmail.com

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Abstract

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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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References

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