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Synthesis 2018; 50(13): 2555-2566
DOI: 10.1055/s-0037-1609687
paper
© Georg Thieme Verlag Stuttgart · New York

A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride

Rui Ding
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Liyuan Lan
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Shuhui Li
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Yongguo Liu
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Shaoxiang Yang
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Hongyu Tian*
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
,
Baoguo Sun*
Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn
› Author AffiliationsFinancial support from the National Key Research and Development Program (2016YFD0400801), Beijing Postdoctoral Research Foundation (2017-22-011), and the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions (CIT&TCD20140306) is gratefully acknowledged.
Further Information

Publication History

Received: 28 February 2018

Accepted after revision: 22 March 2018

Publication Date:
24 April 2018 (online)

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Abstract

A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl+.

Key words

chlorolactonization - alkenoic acids - diphenyl sulfoxide - oxalyl­ chloride - chlorodiphenylsulfonium salt

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609687.
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