Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes
A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐c...
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| Veröffentlicht in: | European journal of organic chemistry 2015-12, Vol.2015 (36), p.8024-8033 |
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| container_issue | 36 |
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| container_title | European journal of organic chemistry |
| container_volume | 2015 |
| creator | Dittrich, Sebastian Bracher, Franz |
| description | A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐cyclopropanes in an unexpected side‐reaction.
Triflimide‐mediated rearrangement of N‐(1‐trimethylsilyl)allylhydrazones gives terminal vinylsilanes through a “traceless bond construction”. A side‐reaction resulting in the formation of cyclopropanes from aromatic hydrazones is described. |
| doi_str_mv | 10.1002/ejoc.201501180 |
| format | Article |
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Triflimide‐mediated rearrangement of N‐(1‐trimethylsilyl)allylhydrazones gives terminal vinylsilanes through a “traceless bond construction”. A side‐reaction resulting in the formation of cyclopropanes from aromatic hydrazones is described.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201501180</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Hydrazones ; Olefination ; Sigmatropic rearrangement ; Silanes ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2015-12, Vol.2015 (36), p.8024-8033</ispartof><rights>Copyright © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3550-639a57b9d0ad48739b74b65787298952c633dd17c0ba78de1efa410bc39e51453</citedby><cites>FETCH-LOGICAL-c3550-639a57b9d0ad48739b74b65787298952c633dd17c0ba78de1efa410bc39e51453</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%2Fejoc.201501180$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201501180$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Dittrich, Sebastian</creatorcontrib><creatorcontrib>Bracher, Franz</creatorcontrib><title>Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐cyclopropanes in an unexpected side‐reaction.
Triflimide‐mediated rearrangement of N‐(1‐trimethylsilyl)allylhydrazones gives terminal vinylsilanes through a “traceless bond construction”. A side‐reaction resulting in the formation of cyclopropanes from aromatic hydrazones is described.</description><subject>Hydrazones</subject><subject>Olefination</subject><subject>Sigmatropic rearrangement</subject><subject>Silanes</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkEFv1DAQRiNEJUrhyjkSFzh4Ga_tOD6iqC2gVStVhVZcLCeesF688dbOCsKZH47TrareuIxH1nv-5K8o3lBYUIDlB9yEbrEEKoDSGp4VxxSUIlApeJ53zjihit2-KF6mtAEAVVX0uPh7HV3v3dZZJI0ZjZ8S2vIKTYxm-IFbHMYy9OUFeUdJRrc4riefnJ_8e-PzXE82mj9hwJSltPdjKt1Qjmssz0LcmtGFYfa_ueFeMzNoBls2U-fDLobdfPOqOOqNT_j64Twpvp6dXjefyOry_HPzcUU6JgSQiikjZKssGMtryVQreVsJWculqpVYdhVj1lLZQWtkbZFibziFtmMKBeWCnRRvD-_m4Ls9plFvwj4OOVJTyWsQwCueqcWB6mJIKWKvd_njJk6agp6b1nPT-rHpLKiD8Mt5nP5D69Mvl81Tlxxcl0b8_eia-FNXkkmhby7O9febq9sGVlQL9g8MIJO3</recordid><startdate>201512</startdate><enddate>201512</enddate><creator>Dittrich, Sebastian</creator><creator>Bracher, Franz</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201512</creationdate><title>Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes</title><author>Dittrich, Sebastian ; Bracher, Franz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3550-639a57b9d0ad48739b74b65787298952c633dd17c0ba78de1efa410bc39e51453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Hydrazones</topic><topic>Olefination</topic><topic>Sigmatropic rearrangement</topic><topic>Silanes</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dittrich, Sebastian</creatorcontrib><creatorcontrib>Bracher, Franz</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dittrich, Sebastian</au><au>Bracher, Franz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2015-12</date><risdate>2015</risdate><volume>2015</volume><issue>36</issue><spage>8024</spage><epage>8033</epage><pages>8024-8033</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A synthesis of terminal vinylsilanes by triflimide‐catalysed rearrangement of N‐(1‐trimethylsilyl)allylhydrazones is reported. This protocol provides a convenient access to versatile olefinic building blocks through a traceless bond construction. Hydrazones derived from aromatic aldehydes give cis‐cyclopropanes in an unexpected side‐reaction.
Triflimide‐mediated rearrangement of N‐(1‐trimethylsilyl)allylhydrazones gives terminal vinylsilanes through a “traceless bond construction”. A side‐reaction resulting in the formation of cyclopropanes from aromatic hydrazones is described.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201501180</doi><tpages>10</tpages></addata></record> |
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| ispartof | European journal of organic chemistry, 2015-12, Vol.2015 (36), p.8024-8033 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Hydrazones Olefination Sigmatropic rearrangement Silanes Synthetic methods |
| title | Triflimide-Catalysed Rearrangement of N-(1-Trimethylsilyl)allylhydrazones Results in the Formation of Vinylsilanes and Cyclopropanes |
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