Chapter 26.SE, Problem 59AP

Interpretation Introduction

Interpretation:

A mechanism for the final step in Edmund degradation- the acid catalyzed rearrangement of the ATZ derivative to the PTH derivative is to be proposed.

Concept introduction:

The various steps in the acid catalyzed rearrangement of the ATZ derivative to the PTH derivative in Edmund degradation are i) Protonation of lactone oxygen ii) Nucleophilic attack of water on the protonated lactone iii) A proton transfer from O to N iv) Opening of the five member ring v) Rotation of the bond and attack by N to form a new five member ring vi) Proton transfer vii) Loss of water viii) Deprotonation.

To propose:

A mechanism for the final step in Edmund degradation- the acid catalyzed rearrangement of the ATZ derivative to the PTH derivative.