An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst
Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydrox...
Gespeichert in:
Veröffentlicht in: | Journal of Oleo Science 2008, Vol.57(8), pp.437-443 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 443 |
---|---|
container_issue | 8 |
container_start_page | 437 |
container_title | Journal of Oleo Science |
container_volume | 57 |
creator | Kasashima, Yoshio Fujimoto, Hiroshi Mino, Takashi Sakamoto, Masami Fujita, Tsutomu |
description | Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement. Spiroethers and bicyclic ethers were also obtained from the corresponding 1,3-diols in yields of over 77%. The most suitable reaction conditions were a temperature of 80°C, a 1:0.2 molar ratio of 1,3-diol:iodine, and a time period of 8 h. In addition, terpenoic ethers were efficiently synthesized from the corresponding 1,3-diols, derived from (+)-camphor and (-)-fenchone, via skeleton rearrangement. In particular, the reaction of the 1,3-diol derived from (+)-camphor proceeded smoothly at room temperature with a yield of 91%. The yield of the cyclic ether using iodine as a catalyst was comparable to the method using sulfuric acid. |
doi_str_mv | 10.5650/jos.57.437 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1444032889</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3106135591</sourcerecordid><originalsourceid>FETCH-LOGICAL-c585t-380f34b0e71699bee36a58632c8e10fea3592a2da92c7a660a88a70e4fb6b9d63</originalsourceid><addsrcrecordid>eNpFUE1P3DAUtKqiQmkv_QGVpd6qZnHs-COnCm13KRKIQ8vZcpxncOTE1M4i7b-vIQtc5lmeeTP2IPSlJisuODkbYl5xuWqYfIdOatbIijFO3z-feaVaLo_Rx5wHQso9lx_Qca0EpTWVJ8ifT3jjnLcephn_2U_zPWSfcXR46x-hGmHsIEGP13sbvMWbwqeMXYojrn-w6pePIePb7Kc7fB0D2F0wCV_G3k-ATcYGr81swj7Pn9CRMyHD58M8Rbfbzd_17-rq5uJyfX5VWa74XDFFHGs6ArIWbdsBMGG4EoxaBTVxYBhvqaG9aamVRghilDKSQOM60bW9YKfo2-L7kOK_HeRZD3GXphKp66ZpCKNKtUX1fVHZFHNO4PRD8qNJe10T_dRq2cqaS11aLeKvB8tdN0L_Jj3UWATbRVBYb02IUyj_fwvuB1m6KYaUEKUJ4fJ5NJoU-wIFaUsEL0Y_F6Mhz-YOXpNMmr0N8PIotcDT8gtj703SMLH_E3Gesw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1444032889</pqid></control><display><type>article</type><title>An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Kasashima, Yoshio ; Fujimoto, Hiroshi ; Mino, Takashi ; Sakamoto, Masami ; Fujita, Tsutomu</creator><creatorcontrib>Kasashima, Yoshio ; Fujimoto, Hiroshi ; Mino, Takashi ; Sakamoto, Masami ; Fujita, Tsutomu ; Graduate School of Science and Technology ; Chiba University ; Education center ; Graduate School of Engineering ; Chiba Institute of Technology ; Faculty of engineering</creatorcontrib><description>Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement. Spiroethers and bicyclic ethers were also obtained from the corresponding 1,3-diols in yields of over 77%. The most suitable reaction conditions were a temperature of 80°C, a 1:0.2 molar ratio of 1,3-diol:iodine, and a time period of 8 h. In addition, terpenoic ethers were efficiently synthesized from the corresponding 1,3-diols, derived from (+)-camphor and (-)-fenchone, via skeleton rearrangement. In particular, the reaction of the 1,3-diol derived from (+)-camphor proceeded smoothly at room temperature with a yield of 91%. The yield of the cyclic ether using iodine as a catalyst was comparable to the method using sulfuric acid.</description><identifier>ISSN: 1345-8957</identifier><identifier>EISSN: 1347-3352</identifier><identifier>DOI: 10.5650/jos.57.437</identifier><identifier>PMID: 18622127</identifier><language>eng</language><publisher>Japan: Japan Oil Chemists' Society</publisher><subject>1,3-diol ; Alcohols - chemistry ; Camphor - chemistry ; Catalysis ; Cyclization ; etherification ; Ethers, Cyclic - chemical synthesis ; five-membered ether ring ; iodine ; Iodine - chemistry ; Magnetic Resonance Spectroscopy ; Models, Chemical ; Solvents - chemistry ; Stereoisomerism ; Temperature ; Time Factors</subject><ispartof>Journal of Oleo Science, 2008, Vol.57(8), pp.437-443</ispartof><rights>2008 by Japan Oil Chemists' Society</rights><rights>Copyright Japan Science and Technology Agency 2008</rights><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c585t-380f34b0e71699bee36a58632c8e10fea3592a2da92c7a660a88a70e4fb6b9d63</citedby><cites>FETCH-LOGICAL-c585t-380f34b0e71699bee36a58632c8e10fea3592a2da92c7a660a88a70e4fb6b9d63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18622127$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kasashima, Yoshio</creatorcontrib><creatorcontrib>Fujimoto, Hiroshi</creatorcontrib><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><creatorcontrib>Fujita, Tsutomu</creatorcontrib><creatorcontrib>Graduate School of Science and Technology</creatorcontrib><creatorcontrib>Chiba University</creatorcontrib><creatorcontrib>Education center</creatorcontrib><creatorcontrib>Graduate School of Engineering</creatorcontrib><creatorcontrib>Chiba Institute of Technology</creatorcontrib><creatorcontrib>Faculty of engineering</creatorcontrib><title>An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst</title><title>Journal of Oleo Science</title><addtitle>J Oleo Sci</addtitle><description>Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement. Spiroethers and bicyclic ethers were also obtained from the corresponding 1,3-diols in yields of over 77%. The most suitable reaction conditions were a temperature of 80°C, a 1:0.2 molar ratio of 1,3-diol:iodine, and a time period of 8 h. In addition, terpenoic ethers were efficiently synthesized from the corresponding 1,3-diols, derived from (+)-camphor and (-)-fenchone, via skeleton rearrangement. In particular, the reaction of the 1,3-diol derived from (+)-camphor proceeded smoothly at room temperature with a yield of 91%. The yield of the cyclic ether using iodine as a catalyst was comparable to the method using sulfuric acid.</description><subject>1,3-diol</subject><subject>Alcohols - chemistry</subject><subject>Camphor - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>etherification</subject><subject>Ethers, Cyclic - chemical synthesis</subject><subject>five-membered ether ring</subject><subject>iodine</subject><subject>Iodine - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Chemical</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><subject>Temperature</subject><subject>Time Factors</subject><issn>1345-8957</issn><issn>1347-3352</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFUE1P3DAUtKqiQmkv_QGVpd6qZnHs-COnCm13KRKIQ8vZcpxncOTE1M4i7b-vIQtc5lmeeTP2IPSlJisuODkbYl5xuWqYfIdOatbIijFO3z-feaVaLo_Rx5wHQso9lx_Qca0EpTWVJ8ifT3jjnLcephn_2U_zPWSfcXR46x-hGmHsIEGP13sbvMWbwqeMXYojrn-w6pePIePb7Kc7fB0D2F0wCV_G3k-ATcYGr81swj7Pn9CRMyHD58M8Rbfbzd_17-rq5uJyfX5VWa74XDFFHGs6ArIWbdsBMGG4EoxaBTVxYBhvqaG9aamVRghilDKSQOM60bW9YKfo2-L7kOK_HeRZD3GXphKp66ZpCKNKtUX1fVHZFHNO4PRD8qNJe10T_dRq2cqaS11aLeKvB8tdN0L_Jj3UWATbRVBYb02IUyj_fwvuB1m6KYaUEKUJ4fJ5NJoU-wIFaUsEL0Y_F6Mhz-YOXpNMmr0N8PIotcDT8gtj703SMLH_E3Gesw</recordid><startdate>2008</startdate><enddate>2008</enddate><creator>Kasashima, Yoshio</creator><creator>Fujimoto, Hiroshi</creator><creator>Mino, Takashi</creator><creator>Sakamoto, Masami</creator><creator>Fujita, Tsutomu</creator><general>Japan Oil Chemists' Society</general><general>Japan Science and Technology Agency</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope></search><sort><creationdate>2008</creationdate><title>An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst</title><author>Kasashima, Yoshio ; Fujimoto, Hiroshi ; Mino, Takashi ; Sakamoto, Masami ; Fujita, Tsutomu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c585t-380f34b0e71699bee36a58632c8e10fea3592a2da92c7a660a88a70e4fb6b9d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>1,3-diol</topic><topic>Alcohols - chemistry</topic><topic>Camphor - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>etherification</topic><topic>Ethers, Cyclic - chemical synthesis</topic><topic>five-membered ether ring</topic><topic>iodine</topic><topic>Iodine - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Chemical</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><topic>Temperature</topic><topic>Time Factors</topic><toplevel>online_resources</toplevel><creatorcontrib>Kasashima, Yoshio</creatorcontrib><creatorcontrib>Fujimoto, Hiroshi</creatorcontrib><creatorcontrib>Mino, Takashi</creatorcontrib><creatorcontrib>Sakamoto, Masami</creatorcontrib><creatorcontrib>Fujita, Tsutomu</creatorcontrib><creatorcontrib>Graduate School of Science and Technology</creatorcontrib><creatorcontrib>Chiba University</creatorcontrib><creatorcontrib>Education center</creatorcontrib><creatorcontrib>Graduate School of Engineering</creatorcontrib><creatorcontrib>Chiba Institute of Technology</creatorcontrib><creatorcontrib>Faculty of engineering</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><jtitle>Journal of Oleo Science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kasashima, Yoshio</au><au>Fujimoto, Hiroshi</au><au>Mino, Takashi</au><au>Sakamoto, Masami</au><au>Fujita, Tsutomu</au><aucorp>Graduate School of Science and Technology</aucorp><aucorp>Chiba University</aucorp><aucorp>Education center</aucorp><aucorp>Graduate School of Engineering</aucorp><aucorp>Chiba Institute of Technology</aucorp><aucorp>Faculty of engineering</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst</atitle><jtitle>Journal of Oleo Science</jtitle><addtitle>J Oleo Sci</addtitle><date>2008</date><risdate>2008</risdate><volume>57</volume><issue>8</issue><spage>437</spage><epage>443</epage><pages>437-443</pages><issn>1345-8957</issn><eissn>1347-3352</eissn><abstract>Intramolecular cyclic etherification of 1,3-diols was investigated using iodine as a catalyst under solution reaction conditions. Compounds containing five-membered ether rings were obtained. Propella ether (11-oxatricyclo[4.4.3.01,6]tridecane) was conveniently synthesized from 1,3-diol (6-(2-hydroxyethyl)spiro[4.5]decan-6-ol) in 97% yield via carbon skeleton rearrangement. Spiroethers and bicyclic ethers were also obtained from the corresponding 1,3-diols in yields of over 77%. The most suitable reaction conditions were a temperature of 80°C, a 1:0.2 molar ratio of 1,3-diol:iodine, and a time period of 8 h. In addition, terpenoic ethers were efficiently synthesized from the corresponding 1,3-diols, derived from (+)-camphor and (-)-fenchone, via skeleton rearrangement. In particular, the reaction of the 1,3-diol derived from (+)-camphor proceeded smoothly at room temperature with a yield of 91%. The yield of the cyclic ether using iodine as a catalyst was comparable to the method using sulfuric acid.</abstract><cop>Japan</cop><pub>Japan Oil Chemists' Society</pub><pmid>18622127</pmid><doi>10.5650/jos.57.437</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1345-8957 |
ispartof | Journal of Oleo Science, 2008, Vol.57(8), pp.437-443 |
issn | 1345-8957 1347-3352 |
language | eng |
recordid | cdi_proquest_journals_1444032889 |
source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
subjects | 1,3-diol Alcohols - chemistry Camphor - chemistry Catalysis Cyclization etherification Ethers, Cyclic - chemical synthesis five-membered ether ring iodine Iodine - chemistry Magnetic Resonance Spectroscopy Models, Chemical Solvents - chemistry Stereoisomerism Temperature Time Factors |
title | An Efficient Synthesis of Five-membered Cyclic Ethers from 1,3-Diols Using Molecular Iodine as a Catalyst |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T15%3A15%3A10IST&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=An%20Efficient%20Synthesis%20of%20Five-membered%20Cyclic%20Ethers%20from%201,3-Diols%20Using%20Molecular%20Iodine%20as%20a%20Catalyst&rft.jtitle=Journal%20of%20Oleo%20Science&rft.au=Kasashima,%20Yoshio&rft.aucorp=Graduate%20School%20of%20Science%20and%20Technology&rft.date=2008&rft.volume=57&rft.issue=8&rft.spage=437&rft.epage=443&rft.pages=437-443&rft.issn=1345-8957&rft.eissn=1347-3352&rft_id=info:doi/10.5650/jos.57.437&rft_dat=%3Cproquest_cross%3E3106135591%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=1444032889&rft_id=info:pmid/18622127&rfr_iscdi=true |