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Reaction of bicyclo[2.2.1]hepta-2,5-diene with the arenesulfenamide-phosphorus(v) oxohalide system: chemo-, regio-, and steroselectivityстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 18 июля 2013 г.
- Авторы: Zyk N.V., Beloglazkina E.K., Belova M.A., Leshcheva I.F., Zefirov N.S.
- Журнал: Russian Chemical Bulletin
- Том: 51
- Номер: 8
- Год издания: 2002
- Издательство: Springer Nature
- Местоположение издательства: Switzerland
- Первая страница: 1468
- Последняя страница: 1477
- DOI: 10.1023/A:1020910906470
- Аннотация: The chemo-, regio- and stereoselectivities of electrophilic sulfenylation of bi-cyclo[2.2.1]hepta-2,5-diene with arenesulfenamides activated by phosphorus(v) oxohalides were studied. The ratio of the products of endo- to exo-attack of the diene by the electrophitic species depends on the solvent nature. The proportions of the products formed upon addition to one double bond and upon homoallylic participation of the second double bond depend on solvent polarity, the nature of the halogen, the substituents in the sulfenamide benzene ring, and on the reaction tune. In addition, the formation of mixed adducts was proven for the reaction carried out in acetonitrile and the formation of disulfenylation products was found in the reaction with excess sulfenylating reagent. Isomerization of exo-3-arylthio-endo-2-halo-bicyclo[2.2.1]hept-5-enes to the products formed with homoallylic participation of the second double bond, exo-5-arylthio-endo-3-halotricyclo[2.2.1.0(2,6)]heptanes, was shown to be possible.
- Добавил в систему: Белоглазкина Елена Кимовна