74261-47-5Relevant academic research and scientific papers
Metal-free oxidative nitration of α-carbon of carbonyls leads to one-pot synthesis of thiohydroximic acids from acetophenones
Dighe, Shashikant U.,Mukhopadhyay, Sushobhan,Priyanka, Kumari,Batra, Sanjay
, p. 4190 - 4193 (2016)
A metal-free nitration of the α-C-H to carbonyl in propiophenones was achieved with I2/NaNO2 in the presence of an oxidant in dimethyl sulfoxide (DMSO) as the medium. Conversely under similar conditions, reaction of acetophenones produced thiohydroximic acids via a radical-based cascade event which involves oxidative nitration of the α-carbon to a carbonyl followed by Michael addition of the thiomethyl group from DMSO and subsequent rearrangement. Besides DMSO, the scope of the reaction encompasses other symmetrical and unsymmetrical dialkylsulfoxides.
1-BENZYL-1,4-DIHYDRONICOTINAMIDE AS A REAGENT FOR REPLACING ALIPHATIC NITRO GROUPS BY HYDROGEN. AN ELECTRON-TRANSFER CHAIN REACTION.
Ono,Tamura,Kaji
, p. 4017 - 4022 (2007/10/02)
The reaction of alpha -nitro nitriles, alpha -nitro esters, and alpha -nitro ketones with 1-benzyl-1,4-dihydronicotinamide (BNAH) can occur with selective replacement of the nitro group by hydrogen without affecting other functional groups. Evidence is presented to support the claim that the reaction proceeds via an electron-transfer chain mechanism in which radical anions and free radicals are intermediates.
