3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity
Autor(a) principal: | |
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Data de Publicação: | 1997 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.1/4237 |
Resumo: | Ethers such as the title compound, C~HIINO3S, (1), rearrange thermally to give N-allyl isomers, (2), in high yield. The X-ray structure determination of the title ether shows a central C--O--C linkage which has one very short (notional) C--O single bond and one exceptionally long single C--O bond. The thermal migration of allyl from the O to the N atom involves the breaking of one of the ether bonds in (1) and a shortening of the other as it becomes a formal carbonyl group in the product (2). The rearrangement is thus considerably assisted by the ground-state structure of the starting ether, in which the bond to be broken is already stretched and the one that is to form a carbonyl group is already a substantial partial double bond. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivityEthers such as the title compound, C~HIINO3S, (1), rearrange thermally to give N-allyl isomers, (2), in high yield. The X-ray structure determination of the title ether shows a central C--O--C linkage which has one very short (notional) C--O single bond and one exceptionally long single C--O bond. The thermal migration of allyl from the O to the N atom involves the breaking of one of the ether bonds in (1) and a shortening of the other as it becomes a formal carbonyl group in the product (2). The rearrangement is thus considerably assisted by the ground-state structure of the starting ether, in which the bond to be broken is already stretched and the one that is to form a carbonyl group is already a substantial partial double bond.International Union of CrystallographySapientiaBarkley, J. V.Cristiano, Maria Lurdes SantosJohnstone, Robert A. W.Loureiro, Rui M. S.2014-06-06T17:32:58Z19972014-06-05T09:15:02Z1997-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.1/4237engBarkley, J. V.; Cristiano, M. L. S.; Johnstone, R. A. W.; Loureiro, R. M. S. 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity, Acta Crystallographica Section C Crystal Structure Communications, 53, 3, 383-386, 1997.0108-2701AUT: MCR00716;info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-24T10:15:30Zoai:sapientia.ualg.pt:10400.1/4237Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:57:41.699060Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
title |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
spellingShingle |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity Barkley, J. V. |
title_short |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
title_full |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
title_fullStr |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
title_full_unstemmed |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
title_sort |
3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity |
author |
Barkley, J. V. |
author_facet |
Barkley, J. V. Cristiano, Maria Lurdes Santos Johnstone, Robert A. W. Loureiro, Rui M. S. |
author_role |
author |
author2 |
Cristiano, Maria Lurdes Santos Johnstone, Robert A. W. Loureiro, Rui M. S. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Sapientia |
dc.contributor.author.fl_str_mv |
Barkley, J. V. Cristiano, Maria Lurdes Santos Johnstone, Robert A. W. Loureiro, Rui M. S. |
description |
Ethers such as the title compound, C~HIINO3S, (1), rearrange thermally to give N-allyl isomers, (2), in high yield. The X-ray structure determination of the title ether shows a central C--O--C linkage which has one very short (notional) C--O single bond and one exceptionally long single C--O bond. The thermal migration of allyl from the O to the N atom involves the breaking of one of the ether bonds in (1) and a shortening of the other as it becomes a formal carbonyl group in the product (2). The rearrangement is thus considerably assisted by the ground-state structure of the starting ether, in which the bond to be broken is already stretched and the one that is to form a carbonyl group is already a substantial partial double bond. |
publishDate |
1997 |
dc.date.none.fl_str_mv |
1997 1997-01-01T00:00:00Z 2014-06-06T17:32:58Z 2014-06-05T09:15:02Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10400.1/4237 |
url |
http://hdl.handle.net/10400.1/4237 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Barkley, J. V.; Cristiano, M. L. S.; Johnstone, R. A. W.; Loureiro, R. M. S. 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity, Acta Crystallographica Section C Crystal Structure Communications, 53, 3, 383-386, 1997. 0108-2701 AUT: MCR00716; |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
International Union of Crystallography |
publisher.none.fl_str_mv |
International Union of Crystallography |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799133189460983808 |