[1 + 2] cycloadditions of sulfur monoxide (SO) to alkenes and alkynes and [1 + 4] cycloadditions to dienes (polyenes). Generation and Reactions of Singlet SO?
[1 + 2] cycloadditions of sulfur monoxide (SO) to alkenes and alkynes and [1 + 4] cycloadditions to dienes (polyenes). Generation and Reactions of Singlet SO?
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DOI：
10.1021/ja072044e
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发表时间：
2007-05
影响因子：
15
通讯作者：
J. Nakayama;Y. Tajima;Pi Xue-hua;Y. Sugihara
中科院分区：
文献类型：
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作者：
J. Nakayama;Y. Tajima;Pi Xue-hua;Y. Sugihara
Diels−桤木加合物是由3，4-二叔丁基噻吩1-氧化物和乙炔二甲酸二甲酯在室温下自发地挤出一氧化硫（SO）而得到的，是一种在温和条件下生成SO的新方法。由此，生成的SO分别与一系列烯烃和炔发生[1 + 2]环加成反应，生成硫杂环丙烷氧化物和硫杂环丙烷1-氧化物，为含硫三元杂环化合物的合成提供了新的途径. SO还与各种环状和非环状二烯反应，得到相应的2，5-二氢噻吩1-氧化物。
The Diels−Alder adduct, produced from 3,4-di-tert-butylthiophene 1-oxide and dimethyl acetylenedicarboxylate, spontaneously extrudes sulfur monoxide (SO) at room temperature and serves as a new method for generation of SO under mild conditions. Thus, the SO generated underwent [1 + 2] cycloadditions to a series of alkenes and alkynes to produce thiirane oxides and thiirene 1-oxides, respectively, providing new syntheses of the sulfur-containing three-membered heterocycles. The SO also reacted with a variety of cyclic and acyclic dienes to give the corresponding 2,5-dihydrothiophene 1-oxides.