SRN1 Synthesis of vic-dinitro compounds containing a nitrodioxane subunit

Abstract

vic-Dinitro compounds containing a nitrodioxane subunit can be obtained by S_RN1 reactions between either open chain gem-chloronitro derivatives as substrates and an anion from nitrodioxane as the nucleophile or ‘reversed’ reagents namely gem-chloronitrodioxane (substrate) and anions from nitro derivatives. The former access is more efficient and is rationalized on the basis that the structure of the radical anion generated by mono electron transfer to the respective substrates allows an appropriate choice of reagents for optimizing the yield of the title compounds to be made.