Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent

doi:10.6023/cjoc202102004

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3330-3334.DOI: 10.6023/cjoc202102004 Previous Articles Next Articles

NOTES

无外加溶剂条件下二甲氨基硫代甲酰氯对亚砜的脱氧还原

王兴越^a^,^b, 许昌林^a, 关宏宇^a^,^*(), 林觅^a, 黄鹏^a^,^*()

a 辽宁大学化学院沈阳 110036
b 中国石油化工股份有限公司大连(抚顺)石油化工研究院辽宁大连 116045

收稿日期:2021-02-01 修回日期:2021-04-16 发布日期:2021-05-14
通讯作者: 关宏宇, 黄鹏
基金资助:
辽宁省教育厅科学研究基金(LYB201606)

Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent

Xingyue Wang^a^,^b, Changlin Xu^a, Hongyu Guan^a(), Mi Lin^a, Peng Huang^a()

a College of Chemistry, Liaoning University, Shenyang 110036
b Dalian (Fushun) Research Institute of Petroleum and Petrochemicals, China Petroleum & Chemical Corporation, Liaoning, Dalian 116045

Received:2021-02-01 Revised:2021-04-16 Published:2021-05-14
Contact: Hongyu Guan, Peng Huang
Supported by:
Scientific Research Funds of Liaoning Education Department(LYB201606)

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Abstract

A simple and effective method of sulfoxide deoxidation is reported. Without any additional solvent, a series of aliphatic and aromatic sulfoxides could react with dimethylthiocarbamoyl chloride at 100 ℃ to afford the corresponding thioethers in moderate to excellent yields. This reaction is compatible with a number of functional groups and is suitable for gram-scale synthesis. A mechanism involving the formation of a thiosulfoxide intermediate and its degradation to thioether and elemental sulfur is proposed for the reaction.

Key words: sulfoxide, thioether, deoxygenation, reduction, thionation

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Xingyue Wang, Changlin Xu, Hongyu Guan, Mi Lin, Peng Huang. Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3330-3334.

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无外加溶剂条件下二甲氨基硫代甲酰氯对亚砜的脱氧还原

Deoxygenation of Sulfoxides with Dimethylthiocarbamoyl Chloride in the Absence of Additional Solvent

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Entry	DMTCC/equiv.	T/℃	Time/h	Yield^b/%
1	1.0	100	2.0	81^c
2	1.0	80	2.0	70^d
3	1.0	120	2.0	81^e
4	1.5	100	0.8	87
5	2.0	100	0.5	92
6	3.0	100	0.5	92

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