Dinitrogen Tetroxide: N₂O₄

Introduction

For over a century, dinitrogen tetroxide has found wide application in organic synthesis, such as nitration of aromatic compounds, [1] nitrosation of amines, [2] preparation of thionitrite [3] and sulfinyl nitrites, [4] oxidation of olefins [5] and dethioacetalization reactions. [6] This compound is commercially supplied at low price in a cylinder, and can be used directly or as liquid (bp 21 ºC), collected by transfer distillation into an ice-cooled vessel. Apart from difficulties in handling the poisonous and corrosive dinitrogen tetroxide, the biggest disadvantage of utilizing gaseous N₂O₄ in organic reactions is its high reactivity which usually causes undesired side reactions. In order to overcome the above mentioned limitations some reports are published on the use of N₂O₄ complexes of organic, [7] polymeric [8] and inorganic compounds [9] as useful reagents in organic reactions.

References and Notes

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