Preparation of some nitro-triesters, and a synthesis of γγ-bis(methoxycarbonyl)-γ-lactones

Abstract

The condensation of dimethyl nitromalonate with methyl acrylate led to either dimethyl α-methoxycarbonyl-α-nitroglutarate or dimethyl 1-methoxycarbonyl-γ-nitropimelate, depending on the nature of the basic catalyst and the conditions. Michael addition of dimethyl nitromalonate to more highly substituted αβ-olefinic esters could not be achieved.

Treatment of three γγ-bis(methoxycarbonyl)-esters with cold fuming nitric acid gave γγ-bis(methoxycarbonyl)-γ-butyrolactones accompanied in two cases by smaller a mounts of the γ-nitro-triesters; a δδ-bis(methoxycarbonyl)-ester gave the δ-hydroxy- and the δ-nitro-triester.