98435-94-0Relevant academic research and scientific papers
Oxidative nitration of alkenes with tert-butyl nitrite and oxygen
Taniguchi, Tsuyoshi,Yajima, Atsushi,Ishibashi, Hiroyuki
supporting information; experimental part, p. 2643 - 2647 (2011/11/30)
A method for the oxidative nitration of alkenes using a combination of tert-butyl nitrite and molecular oxygen to give β-nitro alcohols and their nitrate derivatives has been developed. The present reaction provides a practical method for the synthesis of
Reductive intramolecular Henry reactions induced by Stryker's reagent
Chung, Wing Ki,Chiu, Pauline
, p. 55 - 58 (2007/10/03)
Conjugate reductions of nitroalkenes by Stryker's reagent are ensued by intramolecular aldol reactions to produce β-nitroalcohols in good yield, constituting the first examples of reductive Henry reactions.
Direct synthesis of keto nitroaliphatics via retro-Henry reaction of cyclic 2-nitroalcohols by anhydrous copper sulfate adsorbed on silica gel. A short synthesis of (±)-phoracantholide I
Saikia, Anil K.,Hazarika, Monoj J.,Barua, Nabin C.,Bezbarua, Maitreyee Sarma,Sharma, Ram P.,Ghosh, Anil C.
, p. 981 - 985 (2007/10/03)
It has been observed that anhydrous CuSO4 adsorbed on silica gel effects the C-C bond cleavage between the hydroxy group and the nitro group of 2-nitroalcohols. In the case of 2-nitrocyclohexanols, the products are RCO(CH2)4/su
Reactivity of α-Nitro Ketones toward Organometallic Reagents: Straightforward Synthesis of Tertiary β-Nitroalkanols
Ballini, Roberto,Bartoli, Giuseppe,Gariboldi, Pierluigi V.,Marcantoni, Enrico,Petrini, Marino
, p. 3368 - 3372 (2007/10/02)
Tertiary β-nitro alcohols can be efficiently obtained from the reaction of α-nitro ketones with 2 equiv of an organomagnesium or organolithium reagent.Unexpectedly, Grignard reagents do not deprotonate the α acidic proton of 2 but instead strongly coordinate with the carbonyl and the nitro oxygens.A second equivalent of reagent is thus necessary to carry out the addition.Magnesium reagents fail to react with open-chain α-nitro ketones because a rapid deprotonation occurs, and Grignard reagents are unable to attack monoanion 1.Organolithiums are stronger nucleophiles than organomagnesium reagents and can attack deprotonated substrates.The diastereoselectivity of the reaction depends on the reagent used.Grignard reagents produced almost exclusively trans nitroalkanols with 2, whereas organolithiums show little or no selectivity with the same substrate.Conversely, lithium reagents show excellent stereoselectivity with open-chain substrates and affords the anti diastereomer.
