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Clean and Economic Synthesis of Alkanesulfonyl Chlorides from S-Alkyl Isothiourea Salts via Bleach Oxidative Chlorosulfonation

Zhanhui Yang, Bingnan Zhou, Jiaxi Xu*

*State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China, Email: jxxumail.buct.edu.cn

Z. Yang, B. Zhou, J. Xu, Synthesis, 2014, 46, 225-229.

DOI: 10.1055/s-0033-1338567 (free Supporting Information)


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Abstract

A clean and economic synthesis of alkanesulfonyl chlorides via bleach-mediated oxidative chlorosulfonation of S-alkyl isothiourea salts is simple, environment- and worker-friendly. The procedure uses readily accessible reagents, offers safe operations and easy purification without chromatography, and affords high yields.

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Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation

Z. Yang, J. Xu, Synthesis, 2013, 45, 1675-1682.

Simple Synthesis of Sulfonyl Chlorides from Thiol Precursors and Derivatives by NaClO2-Mediated Oxidative Chlorosulfonation

Z. Yang, Y. Zheng, J. Xu, Synlett, 2013, 24, 2165-2169.


Key Words

sulfonyl chlorides, sodium hypochlorite, S-alkyl isothioureas, chlorosulfonation, oxidation


ID: J66-Y2014