70856-07-4Relevant 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
supporting information, p. 4190 - 4193 (2016/09/09)
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.
Asymmetric Michael addition of α-nitro-ketones using catalytic peptides
Linton, Brian R.,Reutershan, Michael H.,Aderman, Christopher M.,Richardson, Elizabeth A.,Brownell, Kristen R.,Ashley, Charles W.,Evans, Catherine A.,Miller, Scott J.
, p. 1993 - 1997 (2007/10/03)
Peptide-based catalysts have been developed that promote the asymmetric Michael addition of nitroalkanes. The most effective peptides contain a β-turn structural element as well as a basic histidine and an arylsulfonamide-protected arginine. Excellent yields with enantioselectivities of up to 74% ee have been observed.
Facile Preparation of α-Nitroketones from Enol Silyl Ethers
Rathore, Rajendra,Lin, Zhe,Kochi, Jay K.
, p. 1859 - 1862 (2007/10/02)
Treatment of enol silyl ethers with the mild nitrating agent tetranitromethane gives good yields of α-nitroketones at room temperature and below.
