Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors
Autor(a) principal: | |
---|---|
Data de Publicação: | 2005 |
Outros Autores: | , , |
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=S0103-50532005000300013 |
Resumo: | A series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl-4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees of steric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonation of the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,N-dimethylthiocarbamoyl chloride, to obtain the O-arylthiocarbamates. Thermolysis of the latter compounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally, reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed the isolation of the thiophenols. All products were characterized by spectroscopic techniques, and in the case of some of the thiocarbamates the solid state structures were determined by single-crystal X-ray diffraction. |
id |
SBQ-2_5fc0da2adb245d131728da90fd94507b |
---|---|
oai_identifier_str |
oai:scielo:S0103-50532005000300013 |
network_acronym_str |
SBQ-2 |
network_name_str |
Journal of the Brazilian Chemical Society (Online) |
repository_id_str |
|
spelling |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursorsthiolsthiophenolsthiocarbamatesbulky thiolsX-ray structureA series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl-4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees of steric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonation of the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,N-dimethylthiocarbamoyl chloride, to obtain the O-arylthiocarbamates. Thermolysis of the latter compounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally, reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed the isolation of the thiophenols. All products were characterized by spectroscopic techniques, and in the case of some of the thiocarbamates the solid state structures were determined by single-crystal X-ray diffraction.Sociedade Brasileira de Química2005-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000300013Journal of the Brazilian Chemical Society v.16 n.3a 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532005000300013info:eu-repo/semantics/openAccessFlores-Figueroa,AarónArista-M.,VíctorTalancón-Sánchez,DanielCastillo,Ivaneng2005-07-18T00:00:00Zoai:scielo:S0103-50532005000300013Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-07-18T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
title |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
spellingShingle |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors Flores-Figueroa,Aarón thiols thiophenols thiocarbamates bulky thiols X-ray structure |
title_short |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
title_full |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
title_fullStr |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
title_full_unstemmed |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
title_sort |
Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors |
author |
Flores-Figueroa,Aarón |
author_facet |
Flores-Figueroa,Aarón Arista-M.,Víctor Talancón-Sánchez,Daniel Castillo,Ivan |
author_role |
author |
author2 |
Arista-M.,Víctor Talancón-Sánchez,Daniel Castillo,Ivan |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Flores-Figueroa,Aarón Arista-M.,Víctor Talancón-Sánchez,Daniel Castillo,Ivan |
dc.subject.por.fl_str_mv |
thiols thiophenols thiocarbamates bulky thiols X-ray structure |
topic |
thiols thiophenols thiocarbamates bulky thiols X-ray structure |
description |
A series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl-4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees of steric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonation of the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,N-dimethylthiocarbamoyl chloride, to obtain the O-arylthiocarbamates. Thermolysis of the latter compounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally, reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed the isolation of the thiophenols. All products were characterized by spectroscopic techniques, and in the case of some of the thiocarbamates the solid state structures were determined by single-crystal X-ray diffraction. |
publishDate |
2005 |
dc.date.none.fl_str_mv |
2005-06-01 |
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=S0103-50532005000300013 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000300013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532005000300013 |
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.16 n.3a 2005 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 |
_version_ |
1750318166188228608 |