107468-01-9Relevant academic research and scientific papers
Alkylation of Position C-5 of Triacetic Acid Lactone by Sigmatropic Rearrangement of Sulphonium Ylides
March, Pedro de,Moreno-Manas, Marcial,Ripoll, Isabel
, p. 1413 - 1420 (2007/10/02)
Reactions of the 4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-ones 4 with three different diazo compounds under copper or rhodium catalysis give the corresponding sulphonium ylides, which through sigmatropic rearrangement and further prototropy afford the pyrones 6, functionalized at the difficultly accessible position C-5.Desulphurations of products 6 with deactivated Raney nickel give the pyrones 17-19.The influence of the experimental conditions on the competition between sigmatropic and Stevens rearrangement has been studied for the reaction of 4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one (4a) and dimethyl diazomalonate.Several products (9, 10, and 11) arising from sulphonium ylides equilibration and radical recombination have been found in addition to the sigmatropic and the Stevens rearrangement products 6d and 8.
TANDEM SIGMATROPIC REARRANGEMENT OF A SULPHONIUM YLIDE AND CYCLOPROPANATION OF THE RESULTING ELECTRON-RICH OLEFIN ON A 4-METHOXY-2-PYRONE DERIVATIVE
March, P. de,Moreno-Manas, M.,Ripoll, I.,Florencio, F.,Garcia-Blanco, S.,Martinez-Carrera, S.
, p. 3673 - 3674 (2007/10/02)
Rhodium catalyzed reaction of 4-methoxy-6-phenylthiomethyl-2-pyrone with dimethyldiazomalonate affords 5-(bis(methoxycarbonyl))(phenylthio)methyl-4-methoxy-6-methylene-5,6-dihydro-2-pyrone via sigmatropic rearrangement of the corresponding sulphur yl
