The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization
2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier−Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2003-11, Vol.68 (23), p.9148-9150 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 9150 |
|---|---|
| container_issue | 23 |
| container_start_page | 9148 |
| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Liu, Qun Che, Guangbo Yu, Haifeng Liu, Yingchun Zhang, Jingping Zhang, Qian Dong, Dewen |
| description | 2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier−Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79−97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed. |
| doi_str_mv | 10.1021/jo034702t |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71352691</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71352691</sourcerecordid><originalsourceid>FETCH-LOGICAL-a445t-45e9983371f64a37df21a5ff6c4335c1b01bccbbfc27f0ca3111a750a115533c3</originalsourceid><addsrcrecordid>eNptkU9v1DAQxS0EotuFA18A-QISUgMe_0k2x7ZqaaWKVrBcuFgTx1ZdsnFqO4jy6THdVffCXEaa-c3T0xtC3gD7CIzDp7vAhGwYz8_IAhRnVd0y-ZwsGOO8ErwWB-QwpTtWSin1khyArJmUjC2IXd9aeu5jyvRLGPOtD4M3R_S6D3GwKVE4EtVNDBOOtvePa3p2P_tfONgxUxx7epkTPZ6mcobZh5H6ka4Lh8ZmHPyfx-Er8sLhkOzrXV-S7-dn69OL6ur68-Xp8VWFUqpcSWXbdiVEA66WKJrecUDlXG2kEMpAx6Azpuuc4Y1jBgUAYKMYAiglhBFL8n6rO8VwP9uU9cYnY4eh2A9z0g0IxesWCvhhC5oYUorW6Sn6DcYHDUz_y1Q_ZVrYtzvRudvYfk_uQizAux2AyeDgIo7Gpz2neMub8oUlqbacT9n-ftpj_KnrRjRKr2--6R8ngq_U6kJ_3euiScXPHMeS3X8M_gUVG5lK</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71352691</pqid></control><display><type>article</type><title>The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization</title><source>ACS Publications</source><creator>Liu, Qun ; Che, Guangbo ; Yu, Haifeng ; Liu, Yingchun ; Zhang, Jingping ; Zhang, Qian ; Dong, Dewen</creator><creatorcontrib>Liu, Qun ; Che, Guangbo ; Yu, Haifeng ; Liu, Yingchun ; Zhang, Jingping ; Zhang, Qian ; Dong, Dewen</creatorcontrib><description>2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier−Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79−97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034702t</identifier><identifier>PMID: 14604400</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, 2003-11, Vol.68 (23), p.9148-9150</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-45e9983371f64a37df21a5ff6c4335c1b01bccbbfc27f0ca3111a750a115533c3</citedby><cites>FETCH-LOGICAL-a445t-45e9983371f64a37df21a5ff6c4335c1b01bccbbfc27f0ca3111a750a115533c3</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/jo034702t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034702t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15292726$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14604400$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Qun</creatorcontrib><creatorcontrib>Che, Guangbo</creatorcontrib><creatorcontrib>Yu, Haifeng</creatorcontrib><creatorcontrib>Liu, Yingchun</creatorcontrib><creatorcontrib>Zhang, Jingping</creatorcontrib><creatorcontrib>Zhang, Qian</creatorcontrib><creatorcontrib>Dong, Dewen</creatorcontrib><title>The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier−Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79−97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.</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>2003</creationdate><recordtype>article</recordtype><recordid>eNptkU9v1DAQxS0EotuFA18A-QISUgMe_0k2x7ZqaaWKVrBcuFgTx1ZdsnFqO4jy6THdVffCXEaa-c3T0xtC3gD7CIzDp7vAhGwYz8_IAhRnVd0y-ZwsGOO8ErwWB-QwpTtWSin1khyArJmUjC2IXd9aeu5jyvRLGPOtD4M3R_S6D3GwKVE4EtVNDBOOtvePa3p2P_tfONgxUxx7epkTPZ6mcobZh5H6ka4Lh8ZmHPyfx-Er8sLhkOzrXV-S7-dn69OL6ur68-Xp8VWFUqpcSWXbdiVEA66WKJrecUDlXG2kEMpAx6Azpuuc4Y1jBgUAYKMYAiglhBFL8n6rO8VwP9uU9cYnY4eh2A9z0g0IxesWCvhhC5oYUorW6Sn6DcYHDUz_y1Q_ZVrYtzvRudvYfk_uQizAux2AyeDgIo7Gpz2neMub8oUlqbacT9n-ftpj_KnrRjRKr2--6R8ngq_U6kJ_3euiScXPHMeS3X8M_gUVG5lK</recordid><startdate>20031114</startdate><enddate>20031114</enddate><creator>Liu, Qun</creator><creator>Che, Guangbo</creator><creator>Yu, Haifeng</creator><creator>Liu, Yingchun</creator><creator>Zhang, Jingping</creator><creator>Zhang, Qian</creator><creator>Dong, Dewen</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>20031114</creationdate><title>The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization</title><author>Liu, Qun ; Che, Guangbo ; Yu, Haifeng ; Liu, Yingchun ; Zhang, Jingping ; Zhang, Qian ; Dong, Dewen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-45e9983371f64a37df21a5ff6c4335c1b01bccbbfc27f0ca3111a750a115533c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</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>Liu, Qun</creatorcontrib><creatorcontrib>Che, Guangbo</creatorcontrib><creatorcontrib>Yu, Haifeng</creatorcontrib><creatorcontrib>Liu, Yingchun</creatorcontrib><creatorcontrib>Zhang, Jingping</creatorcontrib><creatorcontrib>Zhang, Qian</creatorcontrib><creatorcontrib>Dong, Dewen</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>Liu, Qun</au><au>Che, Guangbo</au><au>Yu, Haifeng</au><au>Liu, Yingchun</au><au>Zhang, Jingping</au><au>Zhang, Qian</au><au>Dong, Dewen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-11-14</date><risdate>2003</risdate><volume>68</volume><issue>23</issue><spage>9148</spage><epage>9150</epage><pages>9148-9150</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier−Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79−97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14604400</pmid><doi>10.1021/jo034702t</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2003-11, Vol.68 (23), p.9148-9150 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71352691 |
| 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 | The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T10%3A46%3A07IST&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=The%20First%20Nonthiolic,%20Odorless%201,3-Propanedithiol%20Equivalent%20and%20Its%20Application%20in%20Thioacetalization&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Liu,%20Qun&rft.date=2003-11-14&rft.volume=68&rft.issue=23&rft.spage=9148&rft.epage=9150&rft.pages=9148-9150&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo034702t&rft_dat=%3Cproquest_cross%3E71352691%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=71352691&rft_id=info:pmid/14604400&rfr_iscdi=true |