Advanced search
Start date
Betweenand


Vinylic tellurides in organic synthesis: obtaining tellurides vinyl chloride and chlorine enínicos/enediínicos systems

Full text
Author(s):
Gilson Rogério Zeni
Total Authors: 1
Document type: Doctoral Thesis
Press: São Paulo.
Institution: Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ)
Defense date:
Examining board members:
Joao Valdir Comasseto; Antonio Luiz Braga; Jonas Gruber; Paulo Roberto Hrihorowitsch Moreno; Jose Augusto Rosario Rodrigues
Advisor: Joao Valdir Comasseto
Abstract

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. (AU)