Formation of new C-O and C-N bonds via base promoted Csp2-Csp3 bond cleavage of α-nitro ketone
A catalyst free protocol has been developed for nucleophilic Csp2-Csp3 bond cleavage of α-nitroketone in the presence of potassium carbonate to create new C-O and C-N bonds. A series of different substituted α-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in the presence of alcohols and bromamine-T, respectively.
Sarma, Manas Jyoti,Borah, Arun Jyoti,Rajbongshi, Kamal Krishna,Phukan, Prodeep
supporting information
p. 7008 - 7011
(2015/11/27)
α-nitro ketone synthesis using N-acylbenzotriazoles
Readily available N-acylbenzotriazoles 2a-1 (derived from a variety of aliphatic, (hetero)aromatic, and N-protected α-amino carboxylic acids) smoothly convert primary 3a-c and α-functionalized primary nitroalkanes 3d into the corresponding α-nitro ketones
Katritzky, Alan R.,Abdel-Fattah, Ashraf A. A.,Gromova, Anna V.,Witek, Rachel,Steel, Peter J.
p. 9211 - 9214
(2007/10/03)
A New Synthetic Method for the Preparation of Ketones by Denitration of α-Nitro Ketones
The sequence of acylation of nitroalkanes and subsequent denitration of the resulting α-nitro ketones provides a new and general method for the preparation of ketones.
Ono, Noboru,Fujii, Masayuki,Kaji, Aritsune
p. 532 - 535
(2007/10/02)
1-BENZYL-1,4-DIHYDRONICOTINAMIDE AS A REAGENT FOR REPLACING ALIPHATIC NITRO GROUPS BY HYDROGEN. AN ELECTRON-TRANSFER CHAIN REACTION.
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.
Ono,Tamura,Kaji
p. 4017 - 4022
(2007/10/02)
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