One-pot synthesis of mixed (Z)-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel beta-organylthio vinyllithium intermediates
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
19/10/2012
19/10/2012
2010
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| Resumo |
One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved. CNPq CAPES Fundacao Araucaria |
| Identificador |
TETRAHEDRON LETTERS, v.51, n.39, p.5141-5145, 2010 0040-4039 http://producao.usp.br/handle/BDPI/20814 10.1016/j.tetlet.2010.07.112 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #Hydrochalcogenation #Transmetallation #Thioacetylenes #beta-Organylthio vinyllithium #STEREOSELECTIVE-SYNTHESIS #VINYLIC TELLURIDES #(E)-VINYLIC SELENIDES #UNSYMMETRICAL 1,4-DIORGANYL-1,3-BUTADIYNES #REGIOSELECTIVE-SYNTHESIS #VERSATILE GENERATION #ORGANIC-SYNTHESIS #TE/LI EXCHANGE #HIGHLY REGIO #HYDROZIRCONATION #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
