NaNO2-ceric ammonium nitrate mediated conversion of acrylic esters and Baylis-Hillman derived acrylic esters into corresponding β-nitro acrylic esters

A variety of acrylic esters, including those derived from Baylis-Hillman reactions, react with NaNO2-ceric ammonium nitrate to form the corresponding beta-nitro alcohols 2 and 5 whose dehydration, via their mesylates, leads to beta-nitro acrylic esters, in good to excellent yields. Further, beta-nitro acrylic esters containing a mesylate group 6, obtained from the Baylis-Hillman products, react with NaN3 to form 2-cyano-3-substituted acrylic esters 10 in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.