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1,3-Dipolar cycloaddition of azomethine ylides generated from aziridines in supercritical carbon dioxide

2006; Elsevier BV; Volume: 47; Issue: 31 Linguagem: Inglês

10.1016/j.tetlet.2006.05.179

1873-3581

Paulo J. S. Gomes, Cláudio M. Nunes, Alberto A. C. C. Pais, Teresa M. V. D. Pinho e Melo, Luı́s G. Arnaut,

Synthesis and Catalytic Reactions

The 1,3-dipolar cycloaddition of azomethine ylides with DMAD in supercritical carbon dioxide is reported. The photolysis reaction conditions were optimized with a suitable adjustment of pressure, temperature, irradiation time and co-solvent concentration leading to a more efficient reaction than in neat acetonitrile. Similar results were observed using thermal reaction conditions. Supercritical carbon dioxide with a minute co-solvent addition is shown to be a very efficient medium for promoting this type of cycloadditions.