PEG-N₂O₄: An Efficient Nitrating Agent for the Selective Mono- and Dinitration of Phenols Under Mild Conditions

Abstract

N₂O₄ was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N₂O₄ (PEG-N₂O₄) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N₂O₄ at room temperature in moderate to high yields.

Keywords:

• Dinitrophenols
• nitration
• nitrophenols
• PEG-N₂O₄

ACKNOWLEDGMENT

Financial support for this work by the Research Affairs Program of Bu-Ali Sina University, Hamedan, Iran, and the Center of Excellence of Developing of Chemical Methods (CEDCM) is gratefully acknowledged.

Notes

^a PEG-N₂O₄–substrate (0.4 g:1 mmol).

^b PEG-N₂O₄–substrate (1.0 g:1 mmol).

^c Isolated yields.

^d The yields and times of dinitration are written in parentheses.

^e Because of volability of the product, CH₂Cl₂ was used as eluent for column chromatography.