30669-80-8Relevant academic research and scientific papers
Detection of an ylide intermediate in the electrochemically-induced Stevens rearrangement of an ammonium salt by in situ UV-vis spectroelectrochemistry
Capobianco, Amedeo,Caruso, Tonino,Palombi, Laura,Peluso, Andrea
, p. 446 - 451 (2013)
The electrochemically-induced Stevens rearrangement of 2-(benzyldimethyl) ammonium acetophenone has been investigated by in situ UV-vis spectroelectrochemistry. Voltammetric analysis and absorption spectra recorded during the potentiostatic reduction indi
Enantioselective [1,2]-Stevens rearrangement using sugar-derived alkoxides as chiral promoters
Tomooka, Katsuhiko,Sakamaki, Junichiro,Harada, Manabu,Wada, Ryoji
, p. 683 - 686 (2008/12/20)
The first example of enantioselective base-induced [1,2]-Stevens rearrangement was achieved by using the newly developed D-glucose-derived lithium alkoxide as a chiral promoter. This rearrangement provides an α-amino ketone having a pseudoquaternary chira
Generation and rearrangements of ylides from tertiary amines and α-diazo ketones - Very high catalytic activity of [RuCl(η5-C5H5)(PPh3) 2]
Del Zotto, Alessandro,Baratta, Walter,Miani, Francesca,Verardo, Giancarlo,Rigo, Pierluigi
, p. 3731 - 3735 (2007/10/03)
The reaction of N,N-dimethyl-2-propen-1-amine, N,N-dimethylbenzylamine and N,N-dimethyl-2-propyn-1-amine with the α-diazo ketones N2CHCOR [R = Me (2a), Et (2b), nPr (2c), iPr (2d), (CH2)10Me (2e), (CH2)14/
One-step synthesis of tertiary α-amino ketones and α-amino esters from amines and diazocarbonyl compounds
West,Glaeske,Naidu
, p. 977 - 980 (2007/10/02)
Diazoketones and diazoesters react with tertiary amines in the presence of copper powder to form transient ammonium ylides. These ylides undergo facile [1,2]-shift from N to C (Stevens rearrangement) of the best migrating group. Overall, α-substituted α-a
Base Catalysed Rearrangements involving Ylide Intermediates. Part 15. The Machanism of the Stevens Rearrangement
Ollis, W. David,Rey, Max,Sutherland, Ian O.
, p. 1009 - 1027 (2007/10/02)
The Stevens rearrangement of acyl-stabilised ammonium ylides has been investigated with regard to stereoselectivity, intramolecularity and the formation of products in addition to the rearrangement product.A detailed study of the effects of reaction conditions upon the rearrangement of the ylide derived from the salt (13) has shown that the stereoselectivity (retention of the configuration of the chiral migrating group) and intramolecularity decrease as solvent viscosity decreases.The rearrangement of the salt (13) in water at 0 deg C is essentially intramolecular with virtually complete retention of the configuration of the migrating group.These results, together with the isolation of products that can be rationalised on the basis of random free-radical coupling, indicate that the rearrangement of acyl-stabilised ammonium ylides normally involves a radical pair mechanism.
Base-catalysed Rearrangements involvung Ylide Intermediates. Part 8. The Preparation and Some Reactions of Stable Ammonium Ylides
Jemison, Robert W.,Mageswaran, Sivapathasuntharam,Ollis, W. David,Sutherland, Ian O.,Thebtaranonth, Yodhathai
, p. 1154 - 1164 (2007/10/02)
The carbonyl-stabilised ammonium ylides (3), (12a-n), and (14a-c) were obtained from the reaction of the corresponding ammonium halides (1), (13a-n), and (15a-c) with sodium hydroxide in water or aqueous methanol.The ylides, which were characterised by their molecular formulae and spectroscopic properies, regenerated quaternary ammonium bromides on treatment with hydrobromic acid.In general the reactions of the ammonium ylides resemble those of the corresponding sulphonium ylides.Thus ylides having a suitable migrating group (ArCH2) undergo a Stevens rearrangement on heating, and other ylides fragment to give a tertiary amine and products containing the PhCOCH grouping.A number of ylides reacted with dimethyl acetylenedicarboxylate to give the furans (32).The ylides (14b and c) with phenyl isocyanate gave the phenylcarbamoyl-substituted ylides.
