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Synthesis 2013; 45(17): 2391-2396
DOI: 10.1055/s-0033-1339351
DOI: 10.1055/s-0033-1339351
paper
Application of Sulfuryl Chloride for the Quick Construction of β-Chlorotetrahydrofuran Derivatives from Homoallylic Alcohols under Mild Conditions
Further Information
Publication History
Received: 28 March 2013
Accepted after revision: 13 June 2013
Publication Date:
22 July 2013 (online)
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%.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For reviews on the halogenation of olefins: