199291-08-2Relevant academic research and scientific papers
Rhodium-catalyzed hydroformylation of 2-vinyl- and 3-vinyl-1-tosylpyrroles as a convenient synthetic route to the corresponding 2-(1-tosylpyrrolyl)propanals and derivatives
Settambolo, Roberta,Caiazzo, Aldo,Lazzaroni, Raffaello
, p. 4111 - 4120 (1997)
2-(1-Tosylpyrrolyl)propanals 2a-b were conveniently prepared (70% yield) via rhodium-catalyzed hydroformylation of the corresponding 2-vinyl- and 3-vinyl-1-tosylpyrroles 1a-b and successfully transformed into some new derivatives (50-90% yield).
Influence of the reaction temperature on the regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles
Caiazzo, Aldo,Settambolo, Roberta,Uccello-Barretta, Gloria,Lazzaroni, Raffaello
, p. 279 - 284 (2007/10/03)
The influence of the temperature on the regioselectivity in the hydroformylation of the vinylpyrrole isomers and of the corresponding N-tosylated substrates has been investigated in the range 20-100°C, in the presence of Rh4(CO)12. At all the temperatures the branched aldehyde was prevailing with respect to the linear isomer for all the substrates ( α-regioselectivity). With increasing temperature, an increase of the linear aldehyde was observed to a different extent in dependence on the substrate nature. 2H NMR investigation of the crude reaction mixture recovered from deuterioformylation of 3-vinylpyrrole at partial substrate conversion points out that the observed depression of the α-regioselectivity with increasing temperature must be connected to a β-hydride elimination process occurring for the branched alkyl-rhodium intermediates but not for the linear ones.
