A short and efficient route from tetrahydrothiophene to thieno[2,3-d][1,3,2]dithiazolium salts

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• 作者：Lidia S. Konstantinova ; Vadim V. Popov ; Andrey V. Lalov ; Ljudmila V. Mikhalchenko ; Vadim P. Gultyai ; Oleg A. Rakitin ; ^{orakitin@ioc.ac.ru}
• 关键词：Sulfur-nitrogen heterocycles ; Fused 1 ; 3 ; 2-dithiazoles ; 1 ; 2 ; 3 ; 4 ; 5-Pentathiepins ; Electrochemical reduction ; EPR spectroscopy
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：18 July, 2012
• 卷：53
• 期：29
• 页码：3767-3770
• 文件大小：690 K

摘要

A synthesis of thieno[2,3-d][1,3,2]dithiazolium salts from commercial tetrahydrothiophene has been developed. The reaction of thieno[2,3-f][1,2,3,4,5]pentathiepin with LiAlH₄ in THF at 鈭?5 掳C, after treatment with acetyl chloride, led to 2,3-(bisacetylthio)thiophene in high yield. Bis(acetylthio)thiophene reacted with sulfuryl chloride and then trimethylsilyl azide was added to afford a 1,3,2-dithiazolium chloride which was converted into a soluble tetrafluoroborate. Electrolytic reduction under controlled potential yielded a thieno[2,3-d][1,3,2]dithiazolyl radical which was characterized by EPR in frozen methylene dichloride.