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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 190, 2015 - Issue 8: 26th International Symposium on Organic Chemistry of Sulfur (ISOCS-26)
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Original Articles

Synthesis of 2-Alkylidene-3,1-Benzoxathiin-4-Ones by the Pummerer Type Reaction

Masaki YamanakaDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan
,
Shigeru ShimadaNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, Japan
,
Wataru AndoNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, Japan
,
Takeo KonakaharaDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan
,
Norio SakaiDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan
&
Masao ShimizuNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, JapanCorrespondence[email protected]
Pages 1307-1308 | Received 09 Jan 2015, Accepted 30 Jan 2015, Published online: 03 Aug 2015
 
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GRAPHICAL ABSTRACT

Abstract

We investigated synthesis of 2-alkylidene-3,1-benzoxathiin-4-ones (2-alkylidene BOTs) from 2-alkyl BOTs with the Pummerer type reaction. The reaction of 2-alkyl BOT 1-oxides, which were obtained by oxidation of 2-alkyl BOTs with mCPBA, with trifluoroacetic anhydride was carried out in the presence of pyridine at 100 °C for 3 h. Consequently, 2-alkylidene BOTs were obtained in 30–88% yields.

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