31436-98-3Relevant academic research and scientific papers
Electron-Transfer Reactions. Oxidation of Grignard Reagents in the Presence of an Aminoxyl as a Radical-Trapping Agent
Carloni, Patricia,Greci, Lucedio,Stipa, Pierluigi,Eberson, Lennart
, p. 4733 - 4737 (2007/10/02)
The indole bisnitrone 1 (E1/2red = -0.125 V vs NHE in DMF) reacts with a series of Grignard reagents (RMgX) including primary, secondary, and tertiary alkyls and benzyl and phenyl derivatives, which show different Eox, by single electron transfer to form C-centered radicals corresponding to the Grignard used.The radicals produced in the reaction were trapped by the (arylimino)indolinone nitroxide 5 to form the alkylated hydroxylamines 6.When the reaction is carried out with a "cyclizing Grignard" such as 5-hexenylmagnesium bromide, the uncyclized (5-hexen-1-yl) 6g and cyclized (methylcyclopentyl) 6h alkylated hydroxylamines are both isolated.In all cases, the Marcus theory treatment predicts high electron-transfer rate constants.
