Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes
Alkylative carbocyclization reactions of Delta *w-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in tetrahydrofuran at 40 degree C followed by ad...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2010-08, Vol.16 (30), p.9164-9174 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9174 |
|---|---|
| container_issue | 30 |
| container_start_page | 9164 |
| container_title | Chemistry : a European journal |
| container_volume | 16 |
| creator | , Toshiro Harada Imaoka, Daisuke Kitano, Chie , Takahiro Kusukawa |
| description | Alkylative carbocyclization reactions of Delta *w-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in tetrahydrofuran at 40 degree C followed by additional stirring at this temperature gives (Z)-3-(1-iodoprop-2-ynylidene)tetrahydrofurans stereoselectively in good to moderate yields. Under similar conditions at 0 degree C, 4-iodobut-1-ynyl tosylates react with 1-alkynyllithium compounds to give (1-iodoprop-2-ynylidene)cyclopropanes. The carbocyclization reactions are proposed to proceed through a new carbenoid-chain process involving the exo cyclization of a lithium acetylide intermediate and the vinylic substitution of the resulting TsO,Li-cycloalkylidenecarbenoids (Ts=tosyl) by 1-alkynyllithium compounds. |
| doi_str_mv | 10.1002/chem.201001105 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_1777994500</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1777994500</sourcerecordid><originalsourceid>FETCH-proquest_miscellaneous_17779945003</originalsourceid><addsrcrecordid>eNqVjs1OwzAQhC0EEuXnynmP5eBiJ02jHKsAAokDh94rE28bg-MtXgcUXo8XIy28AKcZjb6dWSGutJpppbKbpsVulqnRa62KIzHRRaZlXi6KYzFR1byUiyKvTsUZ86tSqlrk-UR8L_3b4E1yHwi1iS_UDI13X2NAAWgDt-iTgU_5SJbMiIbBw4p4f4IMny61sPyN_ehd30FN3Y76YBlWbaR-24I5NGMgZ2XdGhfgOVKDzPCExrqwhUQw1YeNXaSdzOS-0FkMeJ0wRdMONtKmjyYwmGBB7r88sCYgX4iTjfGMl396Lqb3d6v6QY7Ae4-c1p3jBr0fYep5rcuyrKp5oVT-D_QHb8B1XA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1777994500</pqid></control><display><type>article</type><title>Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>, Toshiro Harada ; Imaoka, Daisuke ; Kitano, Chie ; , Takahiro Kusukawa</creator><creatorcontrib>, Toshiro Harada ; Imaoka, Daisuke ; Kitano, Chie ; , Takahiro Kusukawa</creatorcontrib><description>Alkylative carbocyclization reactions of Delta *w-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in tetrahydrofuran at 40 degree C followed by additional stirring at this temperature gives (Z)-3-(1-iodoprop-2-ynylidene)tetrahydrofurans stereoselectively in good to moderate yields. Under similar conditions at 0 degree C, 4-iodobut-1-ynyl tosylates react with 1-alkynyllithium compounds to give (1-iodoprop-2-ynylidene)cyclopropanes. The carbocyclization reactions are proposed to proceed through a new carbenoid-chain process involving the exo cyclization of a lithium acetylide intermediate and the vinylic substitution of the resulting TsO,Li-cycloalkylidenecarbenoids (Ts=tosyl) by 1-alkynyllithium compounds.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201001105</identifier><language>eng</language><subject>Alkylation ; Iodine ; Lithium ; Stirring ; Tetrahydrofuran</subject><ispartof>Chemistry : a European journal, 2010-08, Vol.16 (30), p.9164-9174</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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>, Toshiro Harada</creatorcontrib><creatorcontrib>Imaoka, Daisuke</creatorcontrib><creatorcontrib>Kitano, Chie</creatorcontrib><creatorcontrib>, Takahiro Kusukawa</creatorcontrib><title>Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes</title><title>Chemistry : a European journal</title><description>Alkylative carbocyclization reactions of Delta *w-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in tetrahydrofuran at 40 degree C followed by additional stirring at this temperature gives (Z)-3-(1-iodoprop-2-ynylidene)tetrahydrofurans stereoselectively in good to moderate yields. Under similar conditions at 0 degree C, 4-iodobut-1-ynyl tosylates react with 1-alkynyllithium compounds to give (1-iodoprop-2-ynylidene)cyclopropanes. The carbocyclization reactions are proposed to proceed through a new carbenoid-chain process involving the exo cyclization of a lithium acetylide intermediate and the vinylic substitution of the resulting TsO,Li-cycloalkylidenecarbenoids (Ts=tosyl) by 1-alkynyllithium compounds.</description><subject>Alkylation</subject><subject>Iodine</subject><subject>Lithium</subject><subject>Stirring</subject><subject>Tetrahydrofuran</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqVjs1OwzAQhC0EEuXnynmP5eBiJ02jHKsAAokDh94rE28bg-MtXgcUXo8XIy28AKcZjb6dWSGutJpppbKbpsVulqnRa62KIzHRRaZlXi6KYzFR1byUiyKvTsUZ86tSqlrk-UR8L_3b4E1yHwi1iS_UDI13X2NAAWgDt-iTgU_5SJbMiIbBw4p4f4IMny61sPyN_ehd30FN3Y76YBlWbaR-24I5NGMgZ2XdGhfgOVKDzPCExrqwhUQw1YeNXaSdzOS-0FkMeJ0wRdMONtKmjyYwmGBB7r88sCYgX4iTjfGMl396Lqb3d6v6QY7Ae4-c1p3jBr0fYep5rcuyrKp5oVT-D_QHb8B1XA</recordid><startdate>20100801</startdate><enddate>20100801</enddate><creator>, Toshiro Harada</creator><creator>Imaoka, Daisuke</creator><creator>Kitano, Chie</creator><creator>, Takahiro Kusukawa</creator><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20100801</creationdate><title>Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes</title><author>, Toshiro Harada ; Imaoka, Daisuke ; Kitano, Chie ; , Takahiro Kusukawa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_miscellaneous_17779945003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkylation</topic><topic>Iodine</topic><topic>Lithium</topic><topic>Stirring</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>, Toshiro Harada</creatorcontrib><creatorcontrib>Imaoka, Daisuke</creatorcontrib><creatorcontrib>Kitano, Chie</creatorcontrib><creatorcontrib>, Takahiro Kusukawa</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>, Toshiro Harada</au><au>Imaoka, Daisuke</au><au>Kitano, Chie</au><au>, Takahiro Kusukawa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes</atitle><jtitle>Chemistry : a European journal</jtitle><date>2010-08-01</date><risdate>2010</risdate><volume>16</volume><issue>30</issue><spage>9164</spage><epage>9174</epage><pages>9164-9174</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Alkylative carbocyclization reactions of Delta *w-iodoalkynyl tosylates with alkynyllithium compounds to give products with incorporated iodine atoms are described. Slow addition of 2-(3-iodoprop-2-ynyloxy)ethyl tosylates to 1-alkynyllithium compounds in tetrahydrofuran at 40 degree C followed by additional stirring at this temperature gives (Z)-3-(1-iodoprop-2-ynylidene)tetrahydrofurans stereoselectively in good to moderate yields. Under similar conditions at 0 degree C, 4-iodobut-1-ynyl tosylates react with 1-alkynyllithium compounds to give (1-iodoprop-2-ynylidene)cyclopropanes. The carbocyclization reactions are proposed to proceed through a new carbenoid-chain process involving the exo cyclization of a lithium acetylide intermediate and the vinylic substitution of the resulting TsO,Li-cycloalkylidenecarbenoids (Ts=tosyl) by 1-alkynyllithium compounds.</abstract><doi>10.1002/chem.201001105</doi></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2010-08, Vol.16 (30), p.9164-9174 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1777994500 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkylation Iodine Lithium Stirring Tetrahydrofuran |
| title | Alkylative Carbocyclization of Delta w-Iodoalkynyl Tosylates with Alkynyllithium Compounds Through a Carbenoid-Chain Process Leading to (1-Iodoprop-2-ynylidene)tetrahydrofurans and -cyclopropanes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T23%3A20%3A07IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Alkylative%20Carbocyclization%20of%20Delta%20w-Iodoalkynyl%20Tosylates%20with%20Alkynyllithium%20Compounds%20Through%20a%20Carbenoid-Chain%20Process%20Leading%20to%20(1-Iodoprop-2-ynylidene)tetrahydrofurans%20and%20-cyclopropanes&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=,%20Toshiro%20Harada&rft.date=2010-08-01&rft.volume=16&rft.issue=30&rft.spage=9164&rft.epage=9174&rft.pages=9164-9174&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201001105&rft_dat=%3Cproquest%3E1777994500%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1777994500&rft_id=info:pmid/&rfr_iscdi=true |