1,3-dipolar cycloaddition of nitrones with nitriles: scope and mechanistic study
作者： Pedro H.H. Hermkens , Jan H.v. Maarseveen , Chris G. Kruse , Hans W. Scheeren
DOI: 10.1016/S0040-4020(01)89838-0
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摘要: Abstract 1,3-Dipolar cycloadditions of nitrones 1–6 with nitriles 14–16, proceeded under thermal as well high pressure conditions complete regioselectivity to give Δ4-1,2,4-oxadiazolines 17–19. In general, the cycloaddition seemed be controlled by a HOMO(nitrone)- LUMO(nitrile) interaction. However, crossover in orbital control is probable observed nitrile 16c. Nitrone-nitrile are normal type II so that have U-shaped reactivity curve. Kinetic study on solvent polarity and Hammett equation demonstrated mechanistically nitrone-nitrile consistent nitrone-alkene cycloaddition.
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