Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]

2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Bulletin of the Chemical Society of Japan 2000-03, Vol.73 (3), p.729-737
Hauptverfasser: Ishii, Akihiko, Omata, Takenori, Umezawa, Kazuyo, Nakayama, Juzo
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 737
container_issue 3
container_start_page 729
container_title Bulletin of the Chemical Society of Japan
container_volume 73
creator Ishii, Akihiko
Omata, Takenori
Umezawa, Kazuyo
Nakayama, Juzo
description 2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and trans-isomers take twist and chair conformations, respectively, in the solid state. Variable-temperature 1H NMR spectroscopy in solution showed that the cis-isomer takes a twist conformation exclusively in the temperature range, whereas the trans-isomer exists as an equilibrium mixture of chair and twist conformers. The cis-tetrathiane reacted with Lawesson's reagent at 50 °C to give the corresponding di-2-thianyl disulfide.
doi_str_mv 10.1246/bcsj.73.729
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1459460760</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3130519901</sourcerecordid><originalsourceid>FETCH-LOGICAL-c418t-9babf7b015402a3c8d732963292eb6a2b53bcfd6065b737a98f9cf8cfd405e713</originalsourceid><addsrcrecordid>eNptkE9PwyAchonRxDk9-QWaeNEIEwqF9qiLU5MlHpwnYxpgNO2ylQk0sZ_DLyz7Y7KDByC8PL-H5AXgkuARSRm_U9ovRoKORFocgQGhLEeYU3YMBhjjAqVc0FNw5v0iXvOMFQPwM7FuJUNjW5i8Bdfp0DkDE9nOk1kd0-1TYquEwBQymKGZCU6GupGt8cmHbjzawjFsPaKQo4fGXxNIIIUUhQ28MqHul4gh-23jvq5N2y9VF_rlDfqzhgPr5zk4qeTSm4v9OQTvk8fZ-BlNX59exvdTpBnJAyqUVJVQmGQMp5LqfC5oWvC4UqO4TFVGla7mHPNMCSpkkVeFrvIYMZwZQegQXO28a2e_OuNDubCda-OXJWFZwTgWHEfqdkdpZ713pirXrllJ15cEl5vWy03rpaBlbD3S-Z6uzarR0WV1Y0K_kGvZHvj_Gf0FWtmG-g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1459460760</pqid></control><display><type>article</type><title>Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]</title><source>Oxford University Press Journals All Titles (1996-Current)</source><creator>Ishii, Akihiko ; Omata, Takenori ; Umezawa, Kazuyo ; Nakayama, Juzo</creator><creatorcontrib>Ishii, Akihiko ; Omata, Takenori ; Umezawa, Kazuyo ; Nakayama, Juzo</creatorcontrib><description>2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and trans-isomers take twist and chair conformations, respectively, in the solid state. Variable-temperature 1H NMR spectroscopy in solution showed that the cis-isomer takes a twist conformation exclusively in the temperature range, whereas the trans-isomer exists as an equilibrium mixture of chair and twist conformers. The cis-tetrathiane reacted with Lawesson's reagent at 50 °C to give the corresponding di-2-thianyl disulfide.</description><identifier>ISSN: 0009-2673</identifier><identifier>EISSN: 1348-0634</identifier><identifier>DOI: 10.1246/bcsj.73.729</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><ispartof>Bulletin of the Chemical Society of Japan, 2000-03, Vol.73 (3), p.729-737</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2000</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c418t-9babf7b015402a3c8d732963292eb6a2b53bcfd6065b737a98f9cf8cfd405e713</citedby><cites>FETCH-LOGICAL-c418t-9babf7b015402a3c8d732963292eb6a2b53bcfd6065b737a98f9cf8cfd405e713</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Ishii, Akihiko</creatorcontrib><creatorcontrib>Omata, Takenori</creatorcontrib><creatorcontrib>Umezawa, Kazuyo</creatorcontrib><creatorcontrib>Nakayama, Juzo</creatorcontrib><title>Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]</title><title>Bulletin of the Chemical Society of Japan</title><addtitle>Bulletin of the Chemical Society of Japan</addtitle><description>2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and trans-isomers take twist and chair conformations, respectively, in the solid state. Variable-temperature 1H NMR spectroscopy in solution showed that the cis-isomer takes a twist conformation exclusively in the temperature range, whereas the trans-isomer exists as an equilibrium mixture of chair and twist conformers. The cis-tetrathiane reacted with Lawesson's reagent at 50 °C to give the corresponding di-2-thianyl disulfide.</description><issn>0009-2673</issn><issn>1348-0634</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNptkE9PwyAchonRxDk9-QWaeNEIEwqF9qiLU5MlHpwnYxpgNO2ylQk0sZ_DLyz7Y7KDByC8PL-H5AXgkuARSRm_U9ovRoKORFocgQGhLEeYU3YMBhjjAqVc0FNw5v0iXvOMFQPwM7FuJUNjW5i8Bdfp0DkDE9nOk1kd0-1TYquEwBQymKGZCU6GupGt8cmHbjzawjFsPaKQo4fGXxNIIIUUhQ28MqHul4gh-23jvq5N2y9VF_rlDfqzhgPr5zk4qeTSm4v9OQTvk8fZ-BlNX59exvdTpBnJAyqUVJVQmGQMp5LqfC5oWvC4UqO4TFVGla7mHPNMCSpkkVeFrvIYMZwZQegQXO28a2e_OuNDubCda-OXJWFZwTgWHEfqdkdpZ713pirXrllJ15cEl5vWy03rpaBlbD3S-Z6uzarR0WV1Y0K_kGvZHvj_Gf0FWtmG-g</recordid><startdate>20000301</startdate><enddate>20000301</enddate><creator>Ishii, Akihiko</creator><creator>Omata, Takenori</creator><creator>Umezawa, Kazuyo</creator><creator>Nakayama, Juzo</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20000301</creationdate><title>Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]</title><author>Ishii, Akihiko ; Omata, Takenori ; Umezawa, Kazuyo ; Nakayama, Juzo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c418t-9babf7b015402a3c8d732963292eb6a2b53bcfd6065b737a98f9cf8cfd405e713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ishii, Akihiko</creatorcontrib><creatorcontrib>Omata, Takenori</creatorcontrib><creatorcontrib>Umezawa, Kazuyo</creatorcontrib><creatorcontrib>Nakayama, Juzo</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Bulletin of the Chemical Society of Japan</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ishii, Akihiko</au><au>Omata, Takenori</au><au>Umezawa, Kazuyo</au><au>Nakayama, Juzo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]</atitle><jtitle>Bulletin of the Chemical Society of Japan</jtitle><addtitle>Bulletin of the Chemical Society of Japan</addtitle><date>2000-03-01</date><risdate>2000</risdate><volume>73</volume><issue>3</issue><spage>729</spage><epage>737</epage><pages>729-737</pages><issn>0009-2673</issn><eissn>1348-0634</eissn><abstract>2,2,4,4-Tetramethyl-1-phenyl-6,7-dithiabicyclo[3.1.1]heptane was treated with 2KHSO5·KHSO4·K2SO4 to yield cis- and trans-3,6-bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes. The formation mechanism of the tetrathianes is discussed. X-Ray crystallography disclosed that the cis- and trans-isomers take twist and chair conformations, respectively, in the solid state. Variable-temperature 1H NMR spectroscopy in solution showed that the cis-isomer takes a twist conformation exclusively in the temperature range, whereas the trans-isomer exists as an equilibrium mixture of chair and twist conformers. The cis-tetrathiane reacted with Lawesson's reagent at 50 °C to give the corresponding di-2-thianyl disulfide.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/bcsj.73.729</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0009-2673
ispartof Bulletin of the Chemical Society of Japan, 2000-03, Vol.73 (3), p.729-737
issn 0009-2673
1348-0634
language eng
recordid cdi_proquest_journals_1459460760
source Oxford University Press Journals All Titles (1996-Current)
title Formation, Structure, and Thionation of 1,2,4,5-Tetrathianes [cis- and trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes]
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T22%3A39%3A18IST&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=Formation,%20Structure,%20and%20Thionation%20of%201,2,4,5-Tetrathianes%20%5Bcis-%20and%20trans-3,6-Bis(1,1,3,3-tetramethyl-4-oxo-4-phenylbutyl)-1,2,4,5-tetrathianes%5D&rft.jtitle=Bulletin%20of%20the%20Chemical%20Society%20of%20Japan&rft.au=Ishii,%20Akihiko&rft.date=2000-03-01&rft.volume=73&rft.issue=3&rft.spage=729&rft.epage=737&rft.pages=729-737&rft.issn=0009-2673&rft.eissn=1348-0634&rft_id=info:doi/10.1246/bcsj.73.729&rft_dat=%3Cproquest_cross%3E3130519901%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=1459460760&rft_id=info:pmid/&rfr_iscdi=true