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Formal Insertion of Thioketenes into Donor–Acceptor Cyclopropanes by Lewis Acid Catalysis
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-18 00:00:00 , DOI: 10.1021/acs.orglett.7b03961
André U. Augustin 1 , Marius Busse 1 , Peter G. Jones 1 , Daniel B. Werz 1
Affiliation  

Donor–acceptor cyclopropanes were reacted under Lewis acid catalysis with 3-thioxocyclobutanones as surrogates for disubstituted thioketenes. A broad scope of 2-substituted tetrahydrothiophenes with a semicyclic double bond was obtained under mild conditions with high functional group tolerance and in excellent yield. A sequence of a formal [3 + 2]-cycloaddition followed by the subsequent release of disubstituted ketene is postulated as the mechanism.

中文翻译:

路易斯酸催化将噻吨酮正式插入给体-受体环丙烷中

供体-受体环丙烷在路易斯酸催化下与3-硫代氧代环丁酮作为双取代硫代乙烯酮的代用品反应。在温和的条件下,具有高官能团耐受性和优异的收率,获得了具有半环双键的2-取代四氢噻吩。推测有一个正式的[3 + 2]-环加成序列,然后随后释放出二取代的乙烯酮作为该机理。
更新日期:2018-01-18
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