Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones

Spirocyclic oxetanes were found to undergo versatile transformations under different acid-mediated conditions. Treatment of spirocyclopropyl oxetanes with excess amounts of hydrochloric or hydrobromic acid at room temperature resulted in the formation of spirocyclopropyl fused butenolides with good...

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Veröffentlicht in:RSC advances 2013-01, Vol.3 (20), p.7529-7536
Hauptverfasser: Wu, Dong-Dong, Huang, Cheng-Mei, Wu, Yi-Han, Fun, Hoong-Kun, Xu, Jian-Hua, Zhang, Yan
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container_issue 20
container_start_page 7529
container_title RSC advances
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creator Wu, Dong-Dong
Huang, Cheng-Mei
Wu, Yi-Han
Fun, Hoong-Kun
Xu, Jian-Hua
Zhang, Yan
description Spirocyclic oxetanes were found to undergo versatile transformations under different acid-mediated conditions. Treatment of spirocyclopropyl oxetanes with excess amounts of hydrochloric or hydrobromic acid at room temperature resulted in the formation of spirocyclopropyl fused butenolides with good yields. The transformation of spirocyclopropyl oxetanes mediated by hydroiodic acid led to spirocyclopropyl fused gamma -butyrolactones instead of butenolides. Transformation of spirocyclopropyl oxetanes catalyzed by Lewis acid was also explored and found to give distinct products such as spirobutyl indolinones. The reaction mechanisms involved in the acid-mediated transformations were proposed.
doi_str_mv 10.1039/c3ra00178d
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source Royal Society Of Chemistry Journals 2008-
subjects Formations
Hydrobromic acid
Lewis acid
Reaction mechanisms
Transformations
title Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones
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