The first [2,3]-sigmatropic rearrangement of allylic nitro compounds

Abstract

Allylic nitro compounds 1a–d undergo [2,3]-sigmatropic rearrangement in refluxing 1,2,4-trichlorobenzene, to afford rearranged alcohols 3a–d and carbonyl compounds 4a–d; the heating, under the same conditions, of a mixture of nitroalkenes 7a–c, propargyl alcohols or amine 8 and Bu^tOK promotes a one-pot formation of allylic alcohols 3a–c.