A general synthesis of N-vinyl nitrones |
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Authors: | Denmark Scott E Montgomery Justin I |
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Institution: | Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. |
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Abstract: | A general synthesis of a new type of heterodiene, the N-vinyl nitrone, is described. The synthetic sequence begins with the conjugate addition of benzeneselenol to nitroalkenes (in turn derived from Henry reaction of an aldehyde and a nitroalkane) to provide 2-selenenylnitroalkenes. These selenonitroalkanes are reduced to the corresponding hydroxylamines which are combined with aldehydes to form nitrones. The phenylselenenyl-containing nitrones are then oxidized to selenoxides which undergo syn-selenoxide elimination to provide N-vinyl nitrones. Three X-ray crystal structures of substituted N-vinyl nitrones were obtained. In addition, the first 4+2] cycloaddition of an N-vinyl nitrone is reported. |
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