Synthetic Studies for Novel Structure of α-Nitrogenously Functionalized α-Fluorocarboxylic Acids. II. Synthesis and Some Reactions of α-Fluoro-α-nitrocarboxylic Ester and Carboxamide Derivatives

Abstract

The first synthesis of α-fluoro-α-nitrocarboxamides 11b, c has been achieved by ammonolysis of the corresponding ethyl esters 6b, c. However, α-fluoro-α-nitrocarboxylic acids 8a-c derived from the corresponding esters 6a-c were found to decarboxylate readily to form 1-fluoro-1-nitroalkanes 9a-c. Reduction of the α-fluoro-α-nitrocarboxamide derivatives 11b, c produced the defluorination products 12b, c instead of the desired novel α-fluoro-α-aminocarboxamide 2.