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Synthesis 2013; 45(17): 2391-2396
DOI: 10.1055/s-0033-1339351
paper
© Georg Thieme Verlag Stuttgart · New York

Application of Sulfuryl Chloride for the Quick Construction of β-Chlorotetrahydrofuran Derivatives from Homoallylic Alcohols under Mild Conditions

Xianghua Zeng
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China    Fax: +86(931)8277088   Email: wsun@licp.cas.cn
b   University of Chinese Academy of Sciences, Beijing, 100049, P. R. of China
,
Chengxia Miao
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China    Fax: +86(931)8277088   Email: wsun@licp.cas.cn
,
Shoufeng Wang
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China    Fax: +86(931)8277088   Email: wsun@licp.cas.cn
,
Chungu Xia
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China    Fax: +86(931)8277088   Email: wsun@licp.cas.cn
,
Wei Sun*
a   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China    Fax: +86(931)8277088   Email: wsun@licp.cas.cn
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Further Information

Publication History

Received: 28 March 2013

Accepted after revision: 13 June 2013

Publication Date:
22 July 2013 (online)

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Abstract

An efficient and mild method is reported for the construction of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. The system employs sulfuryl chloride as the chlorinating agent under catalyst-free conditions. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β-chlorotetrahydrofurans in yields up to 98%.

Key words

homoallylic alcohols - sulfuryl chloride - 5-endo cyclization - tetrahydrofuran

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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