1,3-Dipolar cycloadditions of Wang resin supported nitrile oxides have been performed with several dipolarophiles to afford 5-membered heterocycles in fair yields. The nitrile oxides displayed increased stability on the solid phase, allowing clean transformations into nitrosocarbonyl intermediates, which could be trapped with suitable dienes to afford hetero Diels-Alder cycloadducts in moderate yields.
Solid-supported nitrile oxides as stable and valuable reactive intermediates / G. Faita, M. Mella, A. Mortoni, A. Paio, P. Quadrelli, P. Seneci. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 7(2002), pp. 1175-1183. [10.1002/1099-0690(200204)2002:7<1175::AID-EJOC1175>3.0.CO;2-Z]
Solid-supported nitrile oxides as stable and valuable reactive intermediates
P. SeneciUltimo
2002
Abstract
1,3-Dipolar cycloadditions of Wang resin supported nitrile oxides have been performed with several dipolarophiles to afford 5-membered heterocycles in fair yields. The nitrile oxides displayed increased stability on the solid phase, allowing clean transformations into nitrosocarbonyl intermediates, which could be trapped with suitable dienes to afford hetero Diels-Alder cycloadducts in moderate yields.
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