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Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations en route to pyrimidine N-oxides
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-10-17 00:00:00 , DOI: 10.1039/c7ob02463k
Kseniya N. Sedenkova 1, 2, 3, 4, 5 , Elena B. Averina 1, 2, 3, 4, 5 , Yuri K. Grishin 1, 2, 3, 4 , Julia V. Kolodyazhnaya 1, 2, 3, 4 , Victor B. Rybakov 1, 2, 3, 4 , Tamara S. Kuznetsova 1, 2, 3, 4 , Audrey Hughes 6, 7, 8, 9 , Gabriel dos Passos Gomes 6, 7, 8, 9 , Igor V. Alabugin 6, 7, 8, 9 , Nikolay S. Zefirov 1, 2, 3, 4, 5
Affiliation  

Tricyclic bis-adducts of cyclohexa-1,4-diene with bromofluorocarbene and non-symmetric adducts with both bromofluoro- and dichlorocarbenes were synthesised selectively. The treatment of the bis-adducts with nitrating reagents in acetonitrile affords the products of heterocyclization of a sole dihalogenocyclopropane into 4-fluoropyrimidine N-oxide. The difference in the reactivity of bis-cyclopropanes with different sets of halogen substituents leads to selective heterocyclization of bromofluorocyclopropanes without affecting the dichlorocyclopropane moiety.

中文翻译:

取代基对二卤卡宾与环己二烯反应的立体选择性和双二卤代环丙烷在亲电子硝化反应中的反应性(对嘧啶N-氧化物的影响)

选择性地合成了环己-1,4-二烯与溴氟卡宾的三环双加合物以及与溴氟-和二氯卡宾的非对称加合物。在乙腈中用硝化试剂处理双加合物可得到唯一的二卤代环丙烷杂环化成4-氟嘧啶N-氧化物的产物。具有不同组卤素取代基的双环丙烷的反应性差异导致溴氟环丙烷的选择性杂环化而不影响二氯环丙烷部分。
更新日期:2017-11-16
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