Chapter 16.SE, Problem 44MP

Interpretation Introduction

Interpretation:

A mechanism for the Smiles rearrangement reaction shown is to be given.

Concept introduction:

Smiles rearrangement is initiated by the nucleophilic attack of the lone pair of electrons on the N of the amino group on a carbon in the pyridine ring (made electron deficient by the electron attracting nitro group and electronegative N and O atoms). The cleavage of the five member ring formed and subsequent exchange of H⁺ will lead to the formation of the rearranged product.

To propose:

A mechanism for the Smiles rearrangement reaction shown.