Dicubyl Disulfide
Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record...
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| Veröffentlicht in: | Journal of the American Chemical Society 2002-05, Vol.124 (20), p.5626-5627 |
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| container_issue | 20 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 124 |
| creator | Priefer, Ronny Lee, Yoon Joo Barrios, Fabiola Wosnick, Jordan H Lebuis, Anne-Marie Farrell, Patrick G Harpp, David N Sun, Aiming Wu, Shaoxiong Snyder, James P |
| description | Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record (1.771 Å). In contrast to previous generalizations, density functional theory calculations predict a low S−S rotation barrier similar to that for t-BuSSBu-t. Low-temperature 13C NMR (600 MHz) confirms the prediction. |
| doi_str_mv | 10.1021/ja025823y |
| format | Article |
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In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record (1.771 Å). In contrast to previous generalizations, density functional theory calculations predict a low S−S rotation barrier similar to that for t-BuSSBu-t. Low-temperature 13C NMR (600 MHz) confirms the prediction.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja025823y</identifier><identifier>PMID: 12010021</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; Chemistry ; Condensed matter: structure, mechanical and thermal properties ; Exact sciences and technology ; Organic chemistry ; Organic compounds ; Physics ; Preparations and properties ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Journal of the American Chemical Society, 2002-05, Vol.124 (20), p.5626-5627</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a294t-6655f15401a08db3fda44d0bab3b04e73771345247998c7db57a48001e6dccd23</citedby><cites>FETCH-LOGICAL-a294t-6655f15401a08db3fda44d0bab3b04e73771345247998c7db57a48001e6dccd23</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/ja025823y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja025823y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13666451$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12010021$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Priefer, Ronny</creatorcontrib><creatorcontrib>Lee, Yoon Joo</creatorcontrib><creatorcontrib>Barrios, Fabiola</creatorcontrib><creatorcontrib>Wosnick, Jordan H</creatorcontrib><creatorcontrib>Lebuis, Anne-Marie</creatorcontrib><creatorcontrib>Farrell, Patrick G</creatorcontrib><creatorcontrib>Harpp, David N</creatorcontrib><creatorcontrib>Sun, Aiming</creatorcontrib><creatorcontrib>Wu, Shaoxiong</creatorcontrib><creatorcontrib>Snyder, James P</creatorcontrib><title>Dicubyl Disulfide</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record (1.771 Å). In contrast to previous generalizations, density functional theory calculations predict a low S−S rotation barrier similar to that for t-BuSSBu-t. Low-temperature 13C NMR (600 MHz) confirms the prediction.</description><subject>Aliphatic compounds</subject><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNpt0M1KAzEUBeAgiq3VRV9A3Ci4GL35T5faqhUqVqzrkEkykDrt1KQD9u2d0qHduLqE-3G4Jwj1MdxhIPh-boBwRejmCHUxJ5BxTMQx6gIAyaQStIPOUpo3T0YUPkUdTAA3O9xF_VGwdb4pr0Yh1WURnD9HJ4Upk79oZw99PT_NhuNs8v7yOnyYZIYM2DoTgvMCcwbYgHI5LZxhzEFucpoD85JKiSnjhMnBQFnpci4NUwDYC2etI7SHbna5q1j91D6t9SIk68vSLH1VJy2xUFIBbeDtDtpYpRR9oVcxLEzcaAx621_v-zf2sg2t84V3B9kWbsB1C0yypiyiWdqQDo4KIRjfumznQlr73_3exG8tmm5cz6af-nH6MVazyUi_HXKNTXpe1XHZ_N0_B_4BEe56Jw</recordid><startdate>20020522</startdate><enddate>20020522</enddate><creator>Priefer, Ronny</creator><creator>Lee, Yoon Joo</creator><creator>Barrios, Fabiola</creator><creator>Wosnick, Jordan H</creator><creator>Lebuis, Anne-Marie</creator><creator>Farrell, Patrick G</creator><creator>Harpp, David N</creator><creator>Sun, Aiming</creator><creator>Wu, Shaoxiong</creator><creator>Snyder, James P</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>20020522</creationdate><title>Dicubyl Disulfide</title><author>Priefer, Ronny ; Lee, Yoon Joo ; Barrios, Fabiola ; Wosnick, Jordan H ; Lebuis, Anne-Marie ; Farrell, Patrick G ; Harpp, David N ; Sun, Aiming ; Wu, Shaoxiong ; Snyder, James P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a294t-6655f15401a08db3fda44d0bab3b04e73771345247998c7db57a48001e6dccd23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Aliphatic compounds</topic><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Priefer, Ronny</creatorcontrib><creatorcontrib>Lee, Yoon Joo</creatorcontrib><creatorcontrib>Barrios, Fabiola</creatorcontrib><creatorcontrib>Wosnick, Jordan H</creatorcontrib><creatorcontrib>Lebuis, Anne-Marie</creatorcontrib><creatorcontrib>Farrell, Patrick G</creatorcontrib><creatorcontrib>Harpp, David N</creatorcontrib><creatorcontrib>Sun, Aiming</creatorcontrib><creatorcontrib>Wu, Shaoxiong</creatorcontrib><creatorcontrib>Snyder, James P</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Priefer, Ronny</au><au>Lee, Yoon Joo</au><au>Barrios, Fabiola</au><au>Wosnick, Jordan H</au><au>Lebuis, Anne-Marie</au><au>Farrell, Patrick G</au><au>Harpp, David N</au><au>Sun, Aiming</au><au>Wu, Shaoxiong</au><au>Snyder, James P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dicubyl Disulfide</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-05-22</date><risdate>2002</risdate><volume>124</volume><issue>20</issue><spage>5626</spage><epage>5627</epage><pages>5626-5627</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Dicubyl disulfide (1) has been prepared in six steps from commercially available dimethyl-1,4-cubanedicarboxylate in 47% overall yield. In the final step, the previously unknown cubanethiol 2 was oxidized to disulfide 1. X-ray crystallography for 1 reveals the shortest tetragonal C−S bond on record (1.771 Å). In contrast to previous generalizations, density functional theory calculations predict a low S−S rotation barrier similar to that for t-BuSSBu-t. Low-temperature 13C NMR (600 MHz) confirms the prediction.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12010021</pmid><doi>10.1021/ja025823y</doi><tpages>2</tpages></addata></record> |
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| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2002-05, Vol.124 (20), p.5626-5627 |
| issn | 0002-7863 1520-5126 |
| language | eng |
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| source | ACS Publications |
| subjects | Aliphatic compounds Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Organic chemistry Organic compounds Physics Preparations and properties Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Dicubyl Disulfide |
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