Reactions of acceptor substituted thiophene-1,1-dioxides with cyclopentadiene: control of selectivity by substitutionстатья
Статья опубликована в высокорейтинговом журнале
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.
Аннотация:Diels-Aider reactions of thiophene-1, 1-dioxides with strong electron withdrawing groups (EWG) were studied experimentally and theoretically. Thiophene-1, 1-dioxides with two strong EWG behave as dienophiles and regio- and stereoselectively react with cyclopentadiene to give [2 + 4] cycloadducts 2a-c, which are derivatives of benzothiophene. In contrast, thiophene-1, 1-dioxides with one EWG behave as dienes in the inverse electron demand Diels-Alder reaction yielding dihydro-1H-indenes derivatives. Cope [3,3]-sigmatropic rearrangement of adducts 2a-c was also demonstrated. MP2 calculations successfully rationalize the contrasting regioselectivities of these cycloaddition reactions. (c) 2006 Elsevier Ltd. All rights reserved.