Synthetic aspects of free-radical addition reactions. Part VI. The relative reactivities of ethyl malonate and related compounds towards oct-1-ene

Abstract

The overall relative reactivities of ethyl acetoacetate, diethyl malonate, acetylacetone, diethyl ethyl-, butyl-, acetyl-, and cyano-malonates, di-isopropyl malonate, ethyl cyano- and phenyl-acetates, ethyl diacetylacetate, triethoxy-carbonylmethane, and 1,1,2-triethoxycarbonylethane in their radical-induced addition reactions with oct-1-ene to give 1 : 1 adducts have been determined. Ethyl cyanoacetate (12·2) is by far the most reactive (diethyl malonate being taken as unity), while all are much less reactive than carbon tetrachloride (ca. 100).