63044-78-0Relevant academic research and scientific papers
Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis
Uraoka, Saki,Shinohara, Ikumi,Shimizu, Hisato,Noguchi, Keiichi,Yoshimura, Akira,Zhdankin, Viktor V.,Saito, Akio
supporting information, p. 6199 - 6203 (2018/11/10)
As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. Th
Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
Shimizu, Hisato,Yoshimura, Akira,Noguchi, Keiichi,Nemykin, Victor N.,Zhdankin, Viktor V.,Saito, Akio
supporting information, p. 531 - 536 (2018/03/21)
[Bis(trifluoroacetoxy)iodo]benzene (BTI) and (diacetoxyiodo)benzene (DIB) efficiently promote the formation of acylnitroso species from hydroxamic acids in the presence of various dienes to give the corresponding hetero-Diels-Alder (HDA) adducts in moderate to high yields. The present method could be applied to the HDA reactions of acylnitroso species with o-benzoquinones generated by the oxidative dearomatization of guaiacols.
Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: Efficient and practical access to nitroso compounds
Frazier, Charles P.,Bugarin, Alejandro,Engelking, Jarred R.,Read De Alaniz, Javier
experimental part, p. 3620 - 3623 (2012/09/08)
A general and efficient aerobic oxidation of N-substituted hydroxylamines is described. The mild reaction conditions employed provide a catalytic and sustainable alternative to stoichiometric oxidation methods to gain access to a range of nitroso compound
Copper(II)-catalyzed room temperature aerobic oxidation of hydroxamic acids and hydrazides to acyl-nitroso and Azo intermediates, and their Diels-Alder trapping
Chaiyaveij, Duangduan,Cleary, Leah,Batsanov, Andrei S.,Marder, Todd B.,Shea, Kenneth J.,Whiting, Andrew
supporting information; experimental part, p. 3442 - 3445 (2011/08/10)
CuCl2, in the presence of a 2-ethyl-2-oxazoline ligand, is an effective catalyst for the room temperature, aerobic oxidation of hydroxamic acids and hydrazides, to acyl-nitroso and azo dienophiles respectively, which are efficiently trapped in
Development of new transition metal catalysts for the oxidation of a hydroxamic acid with in situ Diels-Alder trapping of the acyl nitroso derivative
Howard, Judith A. K.,Ilyashenko, Gennadiy,Sparkes, Hazel A.,Whiting, Andrew
, p. 2108 - 2111 (2008/02/03)
New transition metal catalysts have been prepared and applied for in situ formation of acyl nitroso dienophiles. The Royal Society of Chemistry.
Formation and Reactions of C-Nitrosoformate Esters, A New Class of Transient Dienophiles
Kirby, Gordon W.,McGuigan, Henry,Mackinnon, John W. M.,McLean, David,Sharma, Ram Prakash
, p. 1437 - 1442 (2007/10/02)
Oxidation of N-hydroxycarbamic esters, ROCONHOH, with tetraethylammonium or sodium periodate in the presence of conjugated dienes gave N-alkoxycarbonyl-3,6-dihydro-2H-1,2-oxazines, formed apparently by cycloaddition of transient C-nitrosoformate esters, ROCONO, with the dienes.Cleavage of various N-alkoxycarbonyl derivatives under mild conditions is exemplified.The cycloadduct (10a) of benzyl nitrosoformate and 9,10-dimethylanthracene decomposed in benzene at 80 deg C in the presence of thebaine (3) to give the corresponding adduct (4a) of thebaine, together with 9,10-dimethylanthracene.Similarly, the adduct (6b) of 2,2,2-trichloroethyl nitrosoformate and cyclopentadiene, when heated with ergosteryl acetate, gave the corrresponding adduct (8b) of the steroid.Benzyl and t-butyl azidoformates decomposed in dimethyl sulphoxide at 115-130 deg C in the presence of thebaine to give the adducts (4a) and (4c) of benzyl and t-butyl nitrosoformate and the alkaloid.The other, major products were the sulphoximides (20a) and (20c).Alkoxycarbonylnitrenes, therefore, attack dimethyl sulphoxide either on sulphur, to give sulphoximides, or on oxygen, to give nitrosoformates.Benzyl nitrosoformate, generated thermally from either the adduct (10a) or (6a), reacted with triphenylphosphine to give, apparently, benzyloxycarbonylnitrene which attacked the solvent, benzene, to form N-benzyloxycarbonylazepine (24a).The adduct (6c) of t-butyl nitrosoformate and cyclopentadiene behaved likewise to give the azepine (24c).The reaction of (6c) with triphenylphosphine in benzene or dichloromethane gave a small quantity of 5,5-dimethyloxazolidin-2-one (26), a known cyclisation product of t-butyloxy-carbonylnitrene.
