36291-55-1Relevant academic research and scientific papers
Synthesis and conjugate addition reactions of N-(β-nitroalkyl)amides
Wade, Peter A.,Paparoidamis, Nicholas,Liao, Jennie,Manor, Brian C.,Debolt, Kristine
, p. 6722 - 6725 (2015)
Nitration of several di- and trisubstituted alkenes with lithium nitrate/TFAA in nitrile solvents afforded N-(β-nitroalkyl)amides in 28-72% yields. Nitration of 1,1-diphenylethene gave 1,1-diphenyl-2-nitroethene in 52% yield instead of the N-(β-nitroalkyl)amide. Reaction of 1-methylcyclohexene using excess lithium nitrate/TFAA in acetonitrile gave a single diastereomer of N-(2,6-dinitro-1-cyclohexyl)acetamide in 55% yield. N-(β-Nitroalkyl)amides underwent diastereoselective Michael addition to a variety of Michael acceptors. Diastereoselectivity is rationalized on the basis of internal hydrogen-bonding within the intermediate nitronate resulting in a strongly-biased Michael donor conformation.
A useful method for the conversion of olefins to nitro olefins
Reddy, G. Sudhakar,Corey
supporting information, p. 3399 - 3402 (2021/05/10)
Triflyl nitrate is easily generated from tetra-n-butylammonium nitrate in CH2Cl2 solution and serves as an effective nitrating agent for a wide range of unsaturated substrates to form nitro olefins.
Acetyl chloride - Silver nitrate - Acetonitrile: A reagent system for the synthesis of 2-nitroglycals and 2-nitro-1-acetamido sugars from glycals
Kancharla, Pavan K.,Reddy, Y. Suman,Dharuman, Suresh,Vankar, Yashwant D.
experimental part, p. 5832 - 5837 (2011/09/20)
A new reagent system comprising acetyl chloride, silver nitrate, and acetonitrile has been developed for the synthesis of 2-nitroglycals from the corresponding glycals. Under certain conditions, the formation of 2-nitro-1-acetamido sugars has also been observed. In addition, a few other non-carbohydrate-derived olefins also gave the corrresponding conjugated nitroolefins.
The Photochemistry of Aliphatic and Alicyclic α,β-Unsaturated Nitro Compounds. A Study of Double Bond Cleavage Following Intramolecular Cyclization and Nitro-Nitrite Rearrangement
Grant, Richard D.,Pinhey, John T.
, p. 1231 - 1244 (2007/10/02)
The light-induced intramolecular cyclization of α,β-unsaturated nitro compounds leading to double bond cleavage, which had previously been detected in a small number of β-nitrostyrenes and α-nitrostilbenes, has been shown to occur in a range of aliphatic and alicyclic α,β-unsaturated nitro compounds.At room temperature the reaction competes to a significant extent with the well known nitro-nitrite rearrangement in the irradiation of 1-nitro-2-phenylcyclohexene (2), 1-methyl-2-nitrocyclohexene (6), 1-methyl-2-nitrocycloheptene (11), 2-methyl-3-nitrobut-2-ene (23)and 2-nitro-3-phenylbut-2-ene (24), while it was the only reaction detected in the case of 1-methyl-2-nitrocyclooctene (12) and 1-nitrocyclooctene (19).No evidence for the cleavage reaction was found with 1-methyl-2-nitrocyclopentene (10), 1-nitrocyclohexene (17), 1-nitrocycloheptene (18) and 3-nitropent-2-ene (25).The nitrile oxides produced in the double bond cleavage reaction were trapped in a cycloaddition with methyl acrylate, yielding 3-substituted methyl 4,5-dihydroisoxazole-5-carboxylates.Irradiations of 1-methyl-2-nitrocyclohexene (6) and 1-methyl-2-nitrocycloheptene (11) in refluxing benzene afforded only the bridged ring isoxazolines (30) and (31) respectively.Syntheses of a number of nitro-olefins are also reported.
