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Polar vs steric effects in the 1,3-dipolar cycloaddition reactions of acetonitrile oxide and 2-endO-acetoxy-5-halo-7-oxabicyclo[2.2.1]hept-5-en-2-exo-carbonitrile |
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| Authors: | Od n Arjona Alfonso de Dios Roberto Fernandez de la Pradilla Araceli Mallo and Joaquin Plumet |
| Institution: | a Departamento de Quimica Organica, Facultad de Quimica, Universidad Complutense, 28040 Madrid Spain b Instituto de Quimica Organica General, C.S.I.C., Juan de la Cierva 3, 28006 Madrid Spain |
| Abstract: | The regioselectivity of the cycloaddition reactions between acetonitrile oxide and a number of 7-oxabicyclo 2.2.1]hept-5-enes is discussed. Acetonitrile oxide adds with complete regioselectivity to 2-endo-acetoxy-5-halo-7-oxabicyclo2.2.1]hept-5-en-2-exo-carbonitriles. Kinetic measurements indicate a more polar transition state for 2a than for the unsubstituted substrate la |
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