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...
Gespeichert in:
Veröffentlicht in: | RSC advances 2013-01, Vol.3 (20), p.7529-7536 |
---|---|
Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 7536 |
---|---|
container_issue | 20 |
container_start_page | 7529 |
container_title | RSC advances |
container_volume | 3 |
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 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1730097103</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1730097103</sourcerecordid><originalsourceid>FETCH-LOGICAL-c264t-dab2b8ee0dd031c1d490d4d9d1277f5c4566de11f8bd266a66c34e34948f88f63</originalsourceid><addsrcrecordid>eNplkM9KxDAQxoMouKx78QlyFKGaNNm09bYs_oMFL3ouaTLBSNrUJAV79ZV8D5_JyAoKzmWGmR8f33wInVJyQQlrLhULkhBa1foALUrCRVES0Rz-mY_RKsYXkkusaSnoAr1vlNVFD9rKBBqnIIdofOhlsn7A3uA42uDVrJwfgx9nh_0bJDlAvMISG6msAyzHfJPqGSf_n--mBIN3VkPEctD486PIqzl4J1XyWegEHRnpIqx--hI93Vw_bu-K3cPt_XazK1QpeCq07MquBiBaE0YV1bwhmutG07KqzFrxtRAaKDV1p0shpBCKcWC84bWpayPYEp3tdbOx1wliansbFTiXv_FTbGnFCGmqHGVGz_eoCj7GAKYdg-1lmFtK2u-s29-s2RfdtXaQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1730097103</pqid></control><display><type>article</type><title>Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones</title><source>Royal Society Of Chemistry Journals 2008-</source><creator>Wu, Dong-Dong ; Huang, Cheng-Mei ; Wu, Yi-Han ; Fun, Hoong-Kun ; Xu, Jian-Hua ; Zhang, Yan</creator><creatorcontrib>Wu, Dong-Dong ; Huang, Cheng-Mei ; Wu, Yi-Han ; Fun, Hoong-Kun ; Xu, Jian-Hua ; Zhang, Yan</creatorcontrib><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.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c3ra00178d</identifier><language>eng</language><subject>Formations ; Hydrobromic acid ; Lewis acid ; Reaction mechanisms ; Transformations</subject><ispartof>RSC advances, 2013-01, Vol.3 (20), p.7529-7536</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c264t-dab2b8ee0dd031c1d490d4d9d1277f5c4566de11f8bd266a66c34e34948f88f63</citedby><cites>FETCH-LOGICAL-c264t-dab2b8ee0dd031c1d490d4d9d1277f5c4566de11f8bd266a66c34e34948f88f63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Wu, Dong-Dong</creatorcontrib><creatorcontrib>Huang, Cheng-Mei</creatorcontrib><creatorcontrib>Wu, Yi-Han</creatorcontrib><creatorcontrib>Fun, Hoong-Kun</creatorcontrib><creatorcontrib>Xu, Jian-Hua</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><title>Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones</title><title>RSC advances</title><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.</description><subject>Formations</subject><subject>Hydrobromic acid</subject><subject>Lewis acid</subject><subject>Reaction mechanisms</subject><subject>Transformations</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNplkM9KxDAQxoMouKx78QlyFKGaNNm09bYs_oMFL3ouaTLBSNrUJAV79ZV8D5_JyAoKzmWGmR8f33wInVJyQQlrLhULkhBa1foALUrCRVES0Rz-mY_RKsYXkkusaSnoAr1vlNVFD9rKBBqnIIdofOhlsn7A3uA42uDVrJwfgx9nh_0bJDlAvMISG6msAyzHfJPqGSf_n--mBIN3VkPEctD486PIqzl4J1XyWegEHRnpIqx--hI93Vw_bu-K3cPt_XazK1QpeCq07MquBiBaE0YV1bwhmutG07KqzFrxtRAaKDV1p0shpBCKcWC84bWpayPYEp3tdbOx1wliansbFTiXv_FTbGnFCGmqHGVGz_eoCj7GAKYdg-1lmFtK2u-s29-s2RfdtXaQ</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Wu, Dong-Dong</creator><creator>Huang, Cheng-Mei</creator><creator>Wu, Yi-Han</creator><creator>Fun, Hoong-Kun</creator><creator>Xu, Jian-Hua</creator><creator>Zhang, Yan</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130101</creationdate><title>Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones</title><author>Wu, Dong-Dong ; Huang, Cheng-Mei ; Wu, Yi-Han ; Fun, Hoong-Kun ; Xu, Jian-Hua ; Zhang, Yan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c264t-dab2b8ee0dd031c1d490d4d9d1277f5c4566de11f8bd266a66c34e34948f88f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Formations</topic><topic>Hydrobromic acid</topic><topic>Lewis acid</topic><topic>Reaction mechanisms</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Dong-Dong</creatorcontrib><creatorcontrib>Huang, Cheng-Mei</creatorcontrib><creatorcontrib>Wu, Yi-Han</creatorcontrib><creatorcontrib>Fun, Hoong-Kun</creatorcontrib><creatorcontrib>Xu, Jian-Hua</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Dong-Dong</au><au>Huang, Cheng-Mei</au><au>Wu, Yi-Han</au><au>Fun, Hoong-Kun</au><au>Xu, Jian-Hua</au><au>Zhang, Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acid-mediated transformation of spirocyclopropyl oxetanes: a facile approach to spirocyclopropyl butenolides and γ-butyrolactones</atitle><jtitle>RSC advances</jtitle><date>2013-01-01</date><risdate>2013</risdate><volume>3</volume><issue>20</issue><spage>7529</spage><epage>7536</epage><pages>7529-7536</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>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.</abstract><doi>10.1039/c3ra00178d</doi><tpages>8</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2046-2069 |
ispartof | RSC advances, 2013-01, Vol.3 (20), p.7529-7536 |
issn | 2046-2069 2046-2069 |
language | eng |
recordid | cdi_proquest_miscellaneous_1730097103 |
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 |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T17%3A36%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Acid-mediated%20transformation%20of%20spirocyclopropyl%20oxetanes:%20a%20facile%20approach%20to%20spirocyclopropyl%20butenolides%20and%20%CE%B3-butyrolactones&rft.jtitle=RSC%20advances&rft.au=Wu,%20Dong-Dong&rft.date=2013-01-01&rft.volume=3&rft.issue=20&rft.spage=7529&rft.epage=7536&rft.pages=7529-7536&rft.issn=2046-2069&rft.eissn=2046-2069&rft_id=info:doi/10.1039/c3ra00178d&rft_dat=%3Cproquest_cross%3E1730097103%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1730097103&rft_id=info:pmid/&rfr_iscdi=true |