Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction
The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methyl...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2005-04, Vol.70 (7), p.2862-2865 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2865 |
|---|---|
| container_issue | 7 |
| container_start_page | 2862 |
| container_title | Journal of organic chemistry |
| container_volume | 70 |
| creator | Miles, William H Dethoff, Elizabeth A Tuson, Hannah H Ulas, Gözde |
| description | The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)2)4/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor−acceptor complex. |
| doi_str_mv | 10.1021/jo0479112 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67552564</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67552564</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-7865a9e8ceb42817dc6cfce959f7636ad942c3a128310a6212f56ecc4f15ef633</originalsourceid><addsrcrecordid>eNptkM1u1DAURi0EotPCghdA2QBCqsE_sR0vUdVOgVZUtEjsLNe5Ji4Zp9hJ1fD0uMqos8EbW_ceH336EHpFyQdKGP14M5BaaUrZE7SighEsNamfohUhjGHOJN9D-znfkHKEEM_RHhWqUaLRKzR9DbmLkN7l6ju0kxvDEKvBVwyfTGnuu7lN9u8QoVqHO8hlfA5jN_cQAbNDjtvwQAx-SjYeVrY6Db-6fi4qW0x3UB2XnyFWY7c8l_kQX6Bn3vYZXm7vA_Tj5Pjq6BSffVt_Pvp0hi1v6IhVI4XV0Di4rllDVeuk8w600F5JLm2ra-a4pazhlFjJKPNCgnO1pwK85PwAvV28t2n4M0EezSZkB31vIwxTNlIJwYSsC_h-AV0ack7gzW0KG5tmQ4l56Ng8dlzY11vpdL2BdkduSy3Amy1gs7O9L924kHeclFwrLQqHFy7kEe4f9zb9LsG4Eubq4tKoC355_qX5adY7r3W55JlSLN39J-A_IsWdow</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67552564</pqid></control><display><type>article</type><title>Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction</title><source>ACS Publications</source><creator>Miles, William H ; Dethoff, Elizabeth A ; Tuson, Hannah H ; Ulas, Gözde</creator><creatorcontrib>Miles, William H ; Dethoff, Elizabeth A ; Tuson, Hannah H ; Ulas, Gözde</creatorcontrib><description>The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)2)4/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor−acceptor complex.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0479112</identifier><identifier>PMID: 15787589</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2005-04, Vol.70 (7), p.2862-2865</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-7865a9e8ceb42817dc6cfce959f7636ad942c3a128310a6212f56ecc4f15ef633</citedby><cites>FETCH-LOGICAL-a381t-7865a9e8ceb42817dc6cfce959f7636ad942c3a128310a6212f56ecc4f15ef633</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo0479112$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0479112$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27080,27928,27929,56742,56792</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16639795$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15787589$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miles, William H</creatorcontrib><creatorcontrib>Dethoff, Elizabeth A</creatorcontrib><creatorcontrib>Tuson, Hannah H</creatorcontrib><creatorcontrib>Ulas, Gözde</creatorcontrib><title>Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)2)4/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor−acceptor complex.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkM1u1DAURi0EotPCghdA2QBCqsE_sR0vUdVOgVZUtEjsLNe5Ji4Zp9hJ1fD0uMqos8EbW_ceH336EHpFyQdKGP14M5BaaUrZE7SighEsNamfohUhjGHOJN9D-znfkHKEEM_RHhWqUaLRKzR9DbmLkN7l6ju0kxvDEKvBVwyfTGnuu7lN9u8QoVqHO8hlfA5jN_cQAbNDjtvwQAx-SjYeVrY6Db-6fi4qW0x3UB2XnyFWY7c8l_kQX6Bn3vYZXm7vA_Tj5Pjq6BSffVt_Pvp0hi1v6IhVI4XV0Di4rllDVeuk8w600F5JLm2ra-a4pazhlFjJKPNCgnO1pwK85PwAvV28t2n4M0EezSZkB31vIwxTNlIJwYSsC_h-AV0ack7gzW0KG5tmQ4l56Ng8dlzY11vpdL2BdkduSy3Amy1gs7O9L924kHeclFwrLQqHFy7kEe4f9zb9LsG4Eubq4tKoC355_qX5adY7r3W55JlSLN39J-A_IsWdow</recordid><startdate>20050401</startdate><enddate>20050401</enddate><creator>Miles, William H</creator><creator>Dethoff, Elizabeth A</creator><creator>Tuson, Hannah H</creator><creator>Ulas, Gözde</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050401</creationdate><title>Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction</title><author>Miles, William H ; Dethoff, Elizabeth A ; Tuson, Hannah H ; Ulas, Gözde</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-7865a9e8ceb42817dc6cfce959f7636ad942c3a128310a6212f56ecc4f15ef633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miles, William H</creatorcontrib><creatorcontrib>Dethoff, Elizabeth A</creatorcontrib><creatorcontrib>Tuson, Hannah H</creatorcontrib><creatorcontrib>Ulas, Gözde</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miles, William H</au><au>Dethoff, Elizabeth A</au><au>Tuson, Hannah H</au><au>Ulas, Gözde</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-04-01</date><risdate>2005</risdate><volume>70</volume><issue>7</issue><spage>2862</spage><epage>2865</epage><pages>2862-2865</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)2)4/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor−acceptor complex.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15787589</pmid><doi>10.1021/jo0479112</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2005-04, Vol.70 (7), p.2862-2865 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67552564 |
| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-17T06%3A35%3A59IST&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=Kishner's%20Reduction%20of%202-Furylhydrazone%20Gives%202-Methylene-2,3-dihydrofuran,%20a%20Highly%20Reactive%20Ene%20in%20the%20Ene%20Reaction&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Miles,%20William%20H&rft.date=2005-04-01&rft.volume=70&rft.issue=7&rft.spage=2862&rft.epage=2865&rft.pages=2862-2865&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo0479112&rft_dat=%3Cproquest_cross%3E67552564%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=67552564&rft_id=info:pmid/15787589&rfr_iscdi=true |