38307-66-3Relevant academic research and scientific papers
Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
, p. 6105 - 6109 (2021/08/18)
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
Stereochemistry of Free-Radical Eliminations on β-Phenylsulfonyl Radicals
Boothe, Thomas E.,Greene, Joseph L.,Shevlin, Philip B.
, p. 794 - 797 (2007/10/02)
Tributyltin radicals have been allowed to react with erythro- and threo-2-bromo-3-(phenylsulfonyl)butane (5a,b) to generate β-(phenylsulfonyl)-sec-butyl radicals 9.The intermediate 9 eliminates phenylsulfonyl radicals to form 2-butenes in a nonstereospecific manner.The lack of stereospecificity is due to rotation about the C2-C3 bond before the loss of the phenylsulfonyl radical can occur and implies that the stabilization of the radical by sulfur bridging is negligible.
