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Doctoral Thesis
DOI
10.11606/T.46.2016.tde-27012016-103927
Document
Author
Full name
Gilson Rogério Zeni
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1999
Supervisor
Committee
Comasseto, Joao Valdir (President)
Braga, Antonio Luiz
Gruber, Jonas
Moreno, Paulo Roberto Hrihorowitsch
Rodrigues, Jose Augusto Rosario
Title in Portuguese
Teluretos vinílicos em síntese orgânica: obtenção de teluretos de cloro vinila e sistemas enínicos/enediínicos
Keywords in Portuguese
Acetilenos Terminais
Acoplamento
Compostos organometálicos
Enediínicos
Enínicos
Paládio
Química orgânica
Síntese orgânica (Química)
Teluretos Vinílicos
Abstract in Portuguese
A primeira parte deste trabalho trata da preparação de teluretos vinílicos funcionalizados, a partir da adição de tricloreto de p-metoxifenil telúrio a hidróxi alcinos e hidróxi alcinos protegidos. Observamos a formação de uma mistura de oxicloretos e dicloretos de aril telúrio. A redução, tanto dos oxicloretos como dicloretos de aril telúrio com tiossulfato de sódio levou a formação dos teluretos vinílicos correspondentes. A segunda parte do trabalho refere-se à síntese de sistemas enínicos e enediínicos. Para tanto, desenvolvemos uma nova metodologia que levam a esses compostos, baseado na reação de acoplamento de um telureto vinílico Z com acetilenos terminais catalisadas por PdCl2/CuI em trietilamina, usando como solvente metanol. Observamos que a reação ocorre com total retenção de configuração da ligação dupla sem interferir com os grupos hidroxilas presentes, tanto no telureto vinílico, quanto no alcino.
Title in English
Vinylic tellurides in organic synthesis: obtaining tellurides vinyl chloride and chlorine enínicos/enediínicos systems
Keywords in English
Acetylenes terminals
Coupling
Enediínos
Enínos
Organic chemistry
Organic synthesis (Chemistry)
Organometallic Compounds
Palladium
Tellurides vinyls
Abstract in English
The first part of this work describes the synthesis of functionalized vinylic tellurides obtained from the addition of aryltellurium trichlorides to protected and unprotected hydroxy-alkynes attempting to determine the regio- and stereochemistry of the obtained tellurides. To that reaction, we observed the formation of a mixture of aryltellurium oxychlorides and dichlorides. The reduction of aryltellurium oxychlorides and dichlorides mixture with sodium thiosulfate yielded the desired vinylic tellurides. The second part of this work describes the synthesis of enyne and enedyine systems. To perform that reaction we developed a new methodology based on the coupling reaction of (Z)-vinylic tellurides and terminal alkynes catalyzed by PdCl2/CuI in triethylamine using methanol as solvent. The desired products were obtained with total retention of configuration of the double bond and the reaction conditions are compatible with hydroxy and carbonyl groups avoiding any protection step.
 
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Publishing Date
2016-01-27
 
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