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Reaction of Electronically Stabilized Thiones with Benzyne. The Isolation of Thiobenzophenone-Benzyne and Thiopivalophenone-Benzyne Adducts

2000; Oxford University Press; Volume: 73; Issue: 1 Linguagem: Inglês

10.1246/bcsj.73.155

1348-0634

Kentaro Okuma, Kyoko Shiki, Shinya Sonoda, Yuji Koga, Kosei Shioji, Tsugio Kitamura, Yuzo Fujiwara, Yoshinobu Yokomori,

Asymmetric Synthesis and Catalysis

Abstract The reaction of thiobenzophenones (1) with phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate (4) in the presence of tetrabutylammonium fluoride afforded the corresponding [4+2] cycloadducts, which are the first examples of thiobenzophenone-benzyne adducts. The reaction of thiopivalophenone (6) with benzyne prepared from 4 and tetrabutylammonium fluoride at room temperature gave [2+2] cycloadducts (7). When the reaction was carried out in refluxing dichloromethane, a mixture of 7 and [4+2] cycloadducts (13) was obtained.