An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement

An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement

We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2005-03, Vol.7 (5), p.783-786
Hauptverfasser: Bendikov, Michael, Duong, Hieu M, Bolanos, Eduardo, Wudl, Fred
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 786
container_issue 5
container_start_page 783
container_title Organic letters
container_volume 7
creator Bendikov, Michael
Duong, Hieu M
Bolanos, Eduardo
Wudl, Fred
description We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).
doi_str_mv 10.1021/ol0477327
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67460783</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67460783</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-dcd059ce732c2e07af7656f9fce879cbc5c9c19de81799cb7ede20435c7508fe3</originalsourceid><addsrcrecordid>eNptkctKAzEUhoMo3he-gGSj4GJqMrfMLKVoFdoKOl0PaeZMG8kkNclU-wI-gI_okzjSUhFcnQvf-eE_P0JnlPQoCem1USRmLArZDjqkSRgFjCTh7rZPyQE6cu6FENpt8n10QBMWsjgmh-jzRuOJhvcFCA8VLt5MMLCmXeCRnFnupdH4QS-NWko9wxw_t6o2eqV5IyvA3uCx9FYqwE_AreV6Bg1o38MjEHOupfNS4GffVhIcNnUnUMzBNlzhMf76-MR9XBi3Un-vT9BezZWD0009RpO726J_HwwfBw_9m2HAIxr5oBIVSXIBnW8RAmG8ZmmS1nktIGO5mIpE5ILmFWSU5d3MoIKQxFEiWEKyGqJjdLnWXVjz2oLzZSOdAKW4BtO6MmVxSlgWdeDVGhTWOGehLhdWNtyuSkrKnwDKbQAde74RbacNVL_k5uMdcLEGuHDli2mt7jz-I_QNUlyPTw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67460783</pqid></control><display><type>article</type><title>An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement</title><source>American Chemical Society Journals</source><creator>Bendikov, Michael ; Duong, Hieu M ; Bolanos, Eduardo ; Wudl, Fred</creator><creatorcontrib>Bendikov, Michael ; Duong, Hieu M ; Bolanos, Eduardo ; Wudl, Fred</creatorcontrib><description>We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0477327</identifier><identifier>PMID: 15727440</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2005-03, Vol.7 (5), p.783-786</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-dcd059ce732c2e07af7656f9fce879cbc5c9c19de81799cb7ede20435c7508fe3</citedby><cites>FETCH-LOGICAL-a313t-dcd059ce732c2e07af7656f9fce879cbc5c9c19de81799cb7ede20435c7508fe3</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/ol0477327$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol0477327$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15727440$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bendikov, Michael</creatorcontrib><creatorcontrib>Duong, Hieu M</creatorcontrib><creatorcontrib>Bolanos, Eduardo</creatorcontrib><creatorcontrib>Wudl, Fred</creatorcontrib><title>An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkctKAzEUhoMo3he-gGSj4GJqMrfMLKVoFdoKOl0PaeZMG8kkNclU-wI-gI_okzjSUhFcnQvf-eE_P0JnlPQoCem1USRmLArZDjqkSRgFjCTh7rZPyQE6cu6FENpt8n10QBMWsjgmh-jzRuOJhvcFCA8VLt5MMLCmXeCRnFnupdH4QS-NWko9wxw_t6o2eqV5IyvA3uCx9FYqwE_AreV6Bg1o38MjEHOupfNS4GffVhIcNnUnUMzBNlzhMf76-MR9XBi3Un-vT9BezZWD0009RpO726J_HwwfBw_9m2HAIxr5oBIVSXIBnW8RAmG8ZmmS1nktIGO5mIpE5ILmFWSU5d3MoIKQxFEiWEKyGqJjdLnWXVjz2oLzZSOdAKW4BtO6MmVxSlgWdeDVGhTWOGehLhdWNtyuSkrKnwDKbQAde74RbacNVL_k5uMdcLEGuHDli2mt7jz-I_QNUlyPTw</recordid><startdate>20050303</startdate><enddate>20050303</enddate><creator>Bendikov, Michael</creator><creator>Duong, Hieu M</creator><creator>Bolanos, Eduardo</creator><creator>Wudl, Fred</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050303</creationdate><title>An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement</title><author>Bendikov, Michael ; Duong, Hieu M ; Bolanos, Eduardo ; Wudl, Fred</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-dcd059ce732c2e07af7656f9fce879cbc5c9c19de81799cb7ede20435c7508fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bendikov, Michael</creatorcontrib><creatorcontrib>Duong, Hieu M</creatorcontrib><creatorcontrib>Bolanos, Eduardo</creatorcontrib><creatorcontrib>Wudl, Fred</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bendikov, Michael</au><au>Duong, Hieu M</au><au>Bolanos, Eduardo</au><au>Wudl, Fred</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-03-03</date><risdate>2005</risdate><volume>7</volume><issue>5</issue><spage>783</spage><epage>786</epage><pages>783-786</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>We report the discovery of the first double-barreled thermal rearrangement of a sulfonynamide and a methoxybenzyl to a nitrile and the first rearrangement of an SO2 group from sulfonamide to ketoimine. The rearrangement occurs under surprisingly mild conditions (onset at 100 °C in the melt).</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15727440</pmid><doi>10.1021/ol0477327</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-03, Vol.7 (5), p.783-786
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_67460783
source American Chemical Society Journals
title An Unexpected Two-Group Migration Involving a Sulfonynamide to Nitrile Rearrangement. Mechanistic Studies of a Thermal N → C Tosyl Rearrangement
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T04%3A14%3A10IST&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=An%20Unexpected%20Two-Group%20Migration%20Involving%20a%20Sulfonynamide%20to%20Nitrile%20Rearrangement.%20Mechanistic%20Studies%20of%20a%20Thermal%20N%20%E2%86%92%20C%20Tosyl%20Rearrangement&rft.jtitle=Organic%20letters&rft.au=Bendikov,%20Michael&rft.date=2005-03-03&rft.volume=7&rft.issue=5&rft.spage=783&rft.epage=786&rft.pages=783-786&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0477327&rft_dat=%3Cproquest_cross%3E67460783%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=67460783&rft_id=info:pmid/15727440&rfr_iscdi=true