Reaction of dithiolactones with benzyne: A novel synthesis of benzo-1,3-dithioles

被引:7
|
作者
Okuma, Kentaro [1 ]
Nojima, Akiko [1 ]
Yokomori, Yoshinobu [2 ]
机构
[1] Fukuoka Univ, Fac Sci, Dept Chem, Jonan Ku, Fukuoka 8140180, Japan
[2] Natl Def Acad, Yokosuka, Kanagawa 2398686, Japan
关键词
benzyne; dithiolactone; benzo-1,3-dithiole; dithiamethylenecyclopropane; 1,2-dithiolane-3-thione;
D O I
10.3987/COM-07-11321
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of benzyne with several kinds of dithiolactones, such as beta-dithiolactone (9), benzothiophene-1-thione (13), 1,2-dithiolane-3-thione (20), and 3,3,5,5-tetramethyl-4-thioxothiolane-2-thione (7), afforded benzo-1,3-dithioles in moderate to good yields, whereas the reaction of benzyne with gamma-thionolactone (16) gave gamma-lactone and diphenyl disulfide.
引用
收藏
页码:1417 / 1424
页数:8
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