36291-55-1Relevant articles and documents
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.
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.