Base-induced decomposition of .beta.-nitroalkyl nitrates

Abstract

The elimination of nitric acid from /3-nitroalkyl nitrates proceeds via an Elcb type of mechanism when the nitro and nitrate groups are attached to primary and secondary carbon atoms, respectively. Where the nitrate function is on a tertiary carbon, it has not been unequivocally shown that an E2 mechanism is operative, although the evidence points in that direction. Previous interpretation of the relative rate differences ascribed to 1,2-dinitrooctadecane, l-nitro-2-octadecyl nitrate, and l-nitro-2-octadecyl nitrite as differences in leaving group abilities may require reconsideration. Most likely these eliminations depend both on the leaving group abilities and on the acidity of the nitromethylene protons.

Synthesis and Antibacterial Activity of Some Novel 4‐Oxopyrido[2,3‐a]phenothiazines

“…Therefore, we sought to introduce an azido group (a nitrene‐generating species) in placement of the 8‐nitro group in compound 3 . In this regard, aromatic‐nitro group substitution by a variety of nucleophiles has been reported in the literature . Accordinly, direct interaction of 3a – d with sodium azide at 55–60°C produced the respective 8‐azido‐7‐(arylthio)‐4‐oxoquinoline‐3‐carboxylates ( 4a – d ).…”

Simultaneous displacement of a nitro group during coupling of diazotized o-nitroaniline with phenols

“…In some cases the nitro group was observed to be a leaving one [2,[23][24][25][26][27][28]. In some reactions the diazonium group had accelerated the elimination of a nitro group [29][30][31].…”