tert-Butyl Hypochlorite Mediated Oxidative Chlorination of S-Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Kui Qiu; Rennan Wang

doi:10.1055/s-0034-1381024

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(20): 3186-3190
DOI: 10.1055/s-0034-1381024

paper

tert-Butyl Hypochlorite Mediated Oxidative Chlorination of S-Alkylisothiourea Salts: Synthesis of Sulfonyl Chlorides

Kui Qiu*

^aSchool of Chemistry and Chemical Engineering, Chongqing University of Science and Technology, Chongqing 401331, P. R. of China eMail: qiucqust@163.com

,

Rennan Wang

^bChina Petroleum Daqing Petrochemical Co. Refinery, Daqing 163000, P. R. of China

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Abstract

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Abstract

Under neutral conditions, a variety of S-alkylisothiourea salts were smoothly converted into the corresponding sulfonyl chlorides through tert-butyl chlorite mediated oxidative chlorination in good to excellent yields after simple purification. In addition to the environmental and procedural advantages of this method, the neutral conditions potentially make it applicable to substrates that bear acid-sensitive functional groups. For example, the Cbz-protected 2-aminoethanesulfonyl chloride could be synthesized in moderate to good yields under the current neutral conditions, and the acid-sensitive Cbz-protecting group was not affected.

Key words

tert-butyl hypochlorite - sulfonyl chlorides - oxidative chlorination - synthesis

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Referenzen

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