Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction

Detalhes bibliográficos
Autor(a) principal: Silva Jr.,Luiz F.
Data de Publicação: 2006
Outros Autores: Quintiliano,Samir A. P., Ferraz,Helena M. C., Santos,Leonardo S., Eberlin,Marcos N.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000500024
Resumo: The oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction.
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spelling Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contractionthallium trinitratering contractionhomoallylic alcoholsfragmentation reactionindanThe oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction.Sociedade Brasileira de Química2006-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000500024Journal of the Brazilian Chemical Society v.17 n.5 2006reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532006000500024info:eu-repo/semantics/openAccessSilva Jr.,Luiz F.Quintiliano,Samir A. P.Ferraz,Helena M. C.Santos,Leonardo S.Eberlin,Marcos N.eng2006-12-01T00:00:00Zoai:scielo:S0103-50532006000500024Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2006-12-01T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
title Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
spellingShingle Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
Silva Jr.,Luiz F.
thallium trinitrate
ring contraction
homoallylic alcohols
fragmentation reaction
indan
title_short Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
title_full Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
title_fullStr Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
title_full_unstemmed Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
title_sort Oxidation of tertiary homoallylic alcohols by thallium trinitrate: fragmentation vs. ring contraction
author Silva Jr.,Luiz F.
author_facet Silva Jr.,Luiz F.
Quintiliano,Samir A. P.
Ferraz,Helena M. C.
Santos,Leonardo S.
Eberlin,Marcos N.
author_role author
author2 Quintiliano,Samir A. P.
Ferraz,Helena M. C.
Santos,Leonardo S.
Eberlin,Marcos N.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Silva Jr.,Luiz F.
Quintiliano,Samir A. P.
Ferraz,Helena M. C.
Santos,Leonardo S.
Eberlin,Marcos N.
dc.subject.por.fl_str_mv thallium trinitrate
ring contraction
homoallylic alcohols
fragmentation reaction
indan
topic thallium trinitrate
ring contraction
homoallylic alcohols
fragmentation reaction
indan
description The oxidation of tertiary homoallylic alcohols with thallium trinitrate (TTN) was investigated. The alcohols bearing an allylic methyl group lose a molecule of acetone via a fragmentation reaction that leads to isomeric secondary allylic alcohols as major products, together with their corresponding acetylated derivatives. On the other hand, treating analogous tertiary alcohols without the allylic methyl group with TTN gives indans, through a ring contraction reaction.
publishDate 2006
dc.date.none.fl_str_mv 2006-10-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000500024
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000500024
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532006000500024
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.17 n.5 2006
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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