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A DFT study on the 1,3-dipolar cycloaddition reactions of C-(hetaryl) nitrones with methyl acrylate and vinyl acetate

AuthorsMerino, Pedro ; Tejero, Tomás ; Chiacchio, Ugo; Romeo, Giovanni; Rescifina, Antonio
Issue Date5-Feb-2007
CitationTetrahedron 63(6): 1448-1458 (2007)
AbstractThe 1,3-dipolar cycloaddition of C-(hetaryl) nitrones with electron-poor and electron-rich alkenes is rationalized. The energetics of the cycloaddition reactions have been investigated through molecular orbital calculations at the B3LYP/6-31-G(d) theory level. By studying different reaction channels and reagent conformations the regio- and stereochemical preferences of the reaction are discussed.
Description11 pages, 8 tables, 6 figures, 2 schemes, 1 chart.
Publisher version (URL)http://dx.doi.org/10.1016/j.tet.2006.11.073
Appears in Collections:(ICMA) Artículos
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