3984-27-8Relevant academic research and scientific papers
Novel electrochemical deoxygenation reaction using diphenylphosphinates
Lam, Kevin,Marko, Istvan E.
supporting information; experimental part, p. 406 - 409 (2011/04/18)
The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time.
Organic electrosynthesis using toluates as simple and versatile radical precursors
Lam, Kevin,Marko, Istvan E.
supporting information; experimental part, p. 95 - 97 (2009/03/11)
The electrolysis of toluate esters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction. The Royal Society of Chemistry.
Toluates: unexpectedly versatile reagents
Lam, Kevin,Markó, István E.
supporting information; experimental part, p. 10930 - 10940 (2010/02/28)
The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted.
Using toluates as simple and versatile radical precursors
Lam, Kevin,Marko, Istvan E.
supporting information; experimental part, p. 2773 - 2776 (2009/05/30)
(Chemical Equation Presented) The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.
Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals
Masaki, Yukio,Miura, Tsuyoshi,Ochiai, Masahito
, p. 195 - 205 (2007/10/03)
A typical π-acid tetracyanoethylene and capto-dative olefin dicyanoketene acetals were found to catalyze stereospecific alcoholysis of epoxides at the ambient temperature to 50°C in good yields. Mildness and significant chemoselectivity of the catalysts were demonstrated by intactness of tetrahydropyranyl ether and ethylene acetal groups. A novel regioselectivity associated with anchimeric assistance of the ethereal group on the side chain was observed in the ring opening reaction of the 1,2-disubstituted epoxides.
Free radical cyclization approach to the hexahydrobenzofuran moiety of avermectins: a model study
Ardisson, J.,Ferezou, J. P.,Julia, M.,Li, Y.,Liu, L. W.,Pancrazi, A.
, p. 387 - 400 (2007/10/02)
Hexahydrobenzofurans were prepared through Bu3SnH radical cyclization of propargyloxy cyclohexanone precursors.Good results were obtained for monosubstituted acetylenic derivatives after conversion of the carbonyl group into the corresponding enol ether.U
Intramolecular Free Radical Cyclisations onto Enol Ethers. A General Synthesis of α-Alkyl-β-oxy- and α-Methylene-β-oxy-γ-butyrolactones
Begley, Michael J.,Landlow, Mark,Pattenden, Gerald
, p. 1095 - 1106 (2007/10/02)
Radical cyclisation of the enol ether bromoacetals (26), (28a-c), (29), and (37) in the presence of tributylstannane, produces precursors to the β-oxy-γ-butyrolactones (33), (34a-c), (35), and the α-methylene-β-oxy-γ-butyrolactone (39) in high overall yields.By contrast, treatment of (26) and (28a-b) with the cobalt(I) reagent derived from bis(dimethylglyoximato)(pyridine)cobalt(III) chloride (40), followed by oxidation of the intermediates (43) leads to the corresponding unsaturated β-oxy-γ-butyrolactones (42).
FREE RADICOL CYCLISATION APPROACH TO THE SOUTHERN MOIETY OF AVERMECTINS.
Ardisson, J.,Ferezou, J. P.,Julia, M.,Pancrazi, A.
, p. 2001 - 2004 (2007/10/02)
A hydroxybenzofuran derivative related to part of the avermectin structure has been prepared by a free radical cyclisation.
