174579-91-0

Upstream product

• 13401-81-5 1-vinyl-1H-pyrrole 
• 201230-82-2 carbon monoxide 
• 85801-33-8 1-(2-iodoethyl)-1H-pyrrole 

Relevant academic research and scientific papers

Intramolecular radical acylation of 2-methylsulfonylpyrroles

Primary alkyl radicals generated (AIBN/Bu3SnH) from 1-(2- or 3- haloalkyl)-2-methylsulfonylpyrroles are intercepted by CO (80 atm), and the acyl radicals so produced undergo intramolecular oxidative cyclization at the α-position, giving bicyclic ketones with retention or loss of the sulfonyl moiety. (C) 2000 Elsevier Science Ltd.

Influence of the reaction temperature on the regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles

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.

High α-regioselectivity in the rhodium-catalyzed hydroformylation of vinylpyrroles

The Rh4(CO)12-catalyzed hydroformylation at low temperature (40°C) of the 1-, 2- and 3-vinylpyrrole gives the corresponding branched aldehydes 2-(1-pyrrolyl)propanal, 2-(2-pyrrolyl)propanal and 2-(3-pyrrolyl)propanal with high α-regioselectivity.