[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone
Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three‐membered ring and ortho‐bisthioquinone. The benzodithioloimine serves...
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| Veröffentlicht in: | Chemistry : a European journal 2016-01, Vol.22 (2), p.521-525 |
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| container_title | Chemistry : a European journal |
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| creator | Garve, Lennart K. B. Pawliczek, Martin Wallbaum, Jan Jones, Peter G. Werz, Daniel B. |
| description | Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three‐membered ring and ortho‐bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X‐ray crystallography. Broad signals in 13C NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature.
Hetero‐[4+3]: Benzodithioloimine bearing two sulfur atoms with strongly amphiphilic character was reacted with donor–acceptor cyclopropanes to give seven‐membered heterocycles in good to excellent yields (see scheme). |
| doi_str_mv | 10.1002/chem.201504013 |
| format | Article |
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Hetero‐[4+3]: Benzodithioloimine bearing two sulfur atoms with strongly amphiphilic character was reacted with donor–acceptor cyclopropanes to give seven‐membered heterocycles in good to excellent yields (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201504013</identifier><identifier>PMID: 26636431</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Bearing ; Chemistry ; Crystallography ; Cycloaddition ; cyclopropanes ; heterocycles ; Lewis acids ; NMR ; Nuclear magnetic resonance ; Organic compounds ; Sulfur ; Temperature effects ; Time ; Transformations ; X-ray crystallography ; X-rays</subject><ispartof>Chemistry : a European journal, 2016-01, Vol.22 (2), p.521-525</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5093-39931c4fffd25c8144d3dd0858d5180f713be591ee191cfc11b8e669005cd4013</citedby><cites>FETCH-LOGICAL-c5093-39931c4fffd25c8144d3dd0858d5180f713be591ee191cfc11b8e669005cd4013</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201504013$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201504013$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26636431$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Garve, Lennart K. B.</creatorcontrib><creatorcontrib>Pawliczek, Martin</creatorcontrib><creatorcontrib>Wallbaum, Jan</creatorcontrib><creatorcontrib>Jones, Peter G.</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><title>[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three‐membered ring and ortho‐bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X‐ray crystallography. Broad signals in 13C NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature.
Hetero‐[4+3]: Benzodithioloimine bearing two sulfur atoms with strongly amphiphilic character was reacted with donor–acceptor cyclopropanes to give seven‐membered heterocycles in good to excellent yields (see scheme).</description><subject>Bearing</subject><subject>Chemistry</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>cyclopropanes</subject><subject>heterocycles</subject><subject>Lewis acids</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic compounds</subject><subject>Sulfur</subject><subject>Temperature effects</subject><subject>Time</subject><subject>Transformations</subject><subject>X-ray crystallography</subject><subject>X-rays</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkV2L1DAUhoMo7rh666UUvBGk4znNR5vL2XGdFdZR2BVBkdBJUydr23STlnUE_7sZug7ihQuBXOR5H87JS8hThDkCZK_01rTzDJADA6T3yAx5hinNBb9PZiBZngpO5RF5FMIVAEhB6UNylAlBBaM4I7--sJf0a7Lc6caVVWUH67rE1clr1zmfLrQ2_eD89N5715edCcmNHbbJou23Np7G6uTEdD9dDG-ta5xtbWeSMiQXo_fuWzmYpI4K54etS09s2FPXo-1cZx6TB3XZBPPk9j4mH9-cXi7P0vP3q7fLxXmqOUiaUikpalbXdZVxXSBjFa0qKHhRcSygzpFuDJdoDErUtUbcFEYICcB1tf-XY_Ji8sYVrkcTBtXaoE3TxHXcGFSUAJOUc3k3mnMWZ2JII_r8H_TKjb6Li6g4B-QZ8Bz-S-WcYpFJUURqPlHauxC8qVXvbVv6nUJQ-6bVvml1aDoGnt1qx01rqgP-p9oIyAm4sY3Z3aFTy7PTd3_L0ykb2zI_DtnSf1cipzlXn9YrxVfry-LDxVp9pr8BtlTDiw</recordid><startdate>20160111</startdate><enddate>20160111</enddate><creator>Garve, Lennart K. 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B.</creatorcontrib><creatorcontrib>Pawliczek, Martin</creatorcontrib><creatorcontrib>Wallbaum, Jan</creatorcontrib><creatorcontrib>Jones, Peter G.</creatorcontrib><creatorcontrib>Werz, Daniel B.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garve, Lennart K. B.</au><au>Pawliczek, Martin</au><au>Wallbaum, Jan</au><au>Jones, Peter G.</au><au>Werz, Daniel B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>[4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-01-11</date><risdate>2016</risdate><volume>22</volume><issue>2</issue><spage>521</spage><epage>525</epage><pages>521-525</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Donor–acceptor cyclopropanes were reacted with amphiphilic benzodithioloimine to give seven‐membered heterocycles with two sulfur atoms. Formally, this transformation can be regarded as a [4+3] cycloaddition reaction of the three‐membered ring and ortho‐bisthioquinone. The benzodithioloimine serves as a surrogate for this highly reactive diene. The structure of the products was confirmed by X‐ray crystallography. Broad signals in 13C NMR studies suggest that several conformers, slowly interconverting on the NMR timescale, are present at room temperature.
Hetero‐[4+3]: Benzodithioloimine bearing two sulfur atoms with strongly amphiphilic character was reacted with donor–acceptor cyclopropanes to give seven‐membered heterocycles in good to excellent yields (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26636431</pmid><doi>10.1002/chem.201504013</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Bearing Chemistry Crystallography Cycloaddition cyclopropanes heterocycles Lewis acids NMR Nuclear magnetic resonance Organic compounds Sulfur Temperature effects Time Transformations X-ray crystallography X-rays |
| title | [4+3] Cycloaddition of Donor-Acceptor Cyclopropanes with Amphiphilic Benzodithioloimine as Surrogate for ortho-Bisthioquinone |
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