Reactions of 4-Methyl-1-(1′-methylethyl)-4-nitrocyclohexa-2,5-dien-1-yl Acetates With Nitrogen Dioxide; Towards a Mechanism for the Formation of Polynitro Cyclohexenyl Esters on Reaction of p-Cymene With Nitrogen Dioxide in Acetic Anhydride

Abstract

The acetoxy nitro diene (21), the C3-epimeric 3,4,6-trinitro-5-nitratocyclohexenes (24) and (25), the 3,6-dinitro-5-nitratocyclohexa-1,3-diene (29), and the 3,6-dinitro-5-acetoxycyclohexa-1,3- diene (32) are identified as probable intermediates in the formation of polynitro cyclohexenyl esters (4)-(13) on reaction of p-cymene with nitrogen dioxide in acetic anhydride; probable reaction pathways are discussed. The X-ray crystal analysis of 4-methyl-1-(1′-methylethy1)-t-5-nitrato-r-3,t-4,c-6-trinitrocyclohexene (24) is reported.