Preparation of 1-nitro-1,3-dienes via nitrotrifluoroacetoxylation of 1,3-dienes

Abstract

1,3-Dienes react with trifluoroacetyl nitrate, generated in situ by reaction of ammonium nitrate with trifluoroacetic anhydride, to give mixtures of 1,2- and 1,4-nitrotrifluoroacetates. Subsequent reaction of these mixtures with a base, e.g. potassium acetate or sodium hydride, affords 1-nitro-1,3-dienes in good yield. Examples of the hydrolysis of the nitrotrifluoroacetates to afford 1,2- and 1,4-nitro alcohols, and of nucleophilic additions to the 1-nitro-1,3-dienes, are given.