ESTUDO ONE-POT DA APLICAÇÃO DO CATALISADOR DE GRUBBS DE PRIMEIRA GERAÇÃO EM REAÇÕES DE METÁTESE DA PIPERINA E EUGENOL: A INFLUÊNCIA DA LIGAÇÃO DUPLA TERMINAL

ONE-POT STUDY OF THE APPLICATION OF CATALYST FIRST-GENERATION GRUBBS IN METATHESIS REACTIONS OF PIPERINE AND EUGENOL: THE INFLUENCE OF THE DOUBLE- BOND TERMINAL

In this paper, the piperine (PIP) and eugenol (EUG) organic compounds were used as substrates in olefin metathesis reactions catalyzed by first-generation Grubbs catalyst (G1) - [RuCl₂(PCy₃)₂(=CHPh)], Cy is cyclohexyl and Ph is phenyl, in a one-pot system. The reactions occurred at 50 ºC, for 24, 48, or 96 h using the two substrates simultaneously in the ratio Ru:PIP:EUG of 1:1:1 and 1:10:10 mol. The results were evaluated by GC-MS, discussed in terms of the electronic and steric characteristics of the G1, and the structural proprieties of the substrates. In the Ru:PIP:EUG ratio of 1:1:1 mol, a dimeric species was observed for the olefin metathesis of EUG, in all time studied and in an additional experiment at 70 ºC for 48 h. When the Ru:PIP:EUG ratio was 1:10:10 mol, this dimer was not observed. Isomerization processes also were observed at all temperatures and catalyst:substrates ratio. The reaction yield increased with the raise of substrates amount. There was no cross-metathesis reaction. This fact was attributed to the chelating effect of the double coordination of the PIP to the catalyst.

Keywords:
olefin metathesis; Grubbs catalysts; piperine; eugenol.