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Synthesis 2017; 49(23): 5258-5262
DOI: 10.1055/s-0036-1588545
paper
© Georg Thieme Verlag Stuttgart · New York

Base-Promoted Synthesis of O-Aryl/Alkyl N,N-Dimethylthiocarbamates Starting from Inexpensive and Environmentally Benign Disulfide

Zhi-Bing Dong*
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
b   Key Laboratory of Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430205, P. R. of China   eMail: dzb04982@wit.edu.cn
,
Ming Wang
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Hui Zhu
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Xing Liu
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
,
Cai-Zhu Chang
a   School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, P. R. of China
› InstitutsangabenWe thank the foundation support from National Natural Science Foundation of China (21302150), Hubei Provincial Department of Education (D20131501), Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry [2012]1707, foundation of Chutian distinguished fellow from Hubei Provincial Department of Education, foundation of High-end Talent Cultivation Program from Wuhan Institute of Technology.
Weitere Informationen

Publikationsverlauf

Received: 29. Juni 2017

Accepted after revision: 19. Juli 2017

Publikationsdatum:
22. August 2017 (online)

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Abstract

A series of O-aryl (alkyl) N,N-dimethylthiocarbamates were synthesized in good yields (70–77%) by reacting substituted phenols or alkyl alcohol with inexpensive, stable, and environmentally benign tetramethylthiuram disulfide (TMTD) in the presence of NaH. By avoiding use of the toxic and corrosive N,N-dialkylthiocarbamoyl chloride, the method provides a green and facile preparation for some important precursors of potentially biologically reactive compounds.

Key words

thiocarbamate - disulfide - phenols - sodium hydride - synthetic methods

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588545.
  • Supporting Information
 

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