Synthesis, Characterization of Cellulose Grafted N-Oxide Reagent and Its Application in Oxidation of Alkyl/Aryl Halides

Inderjeet Kaur,Poonam K Dhiman

doi:10.4236/ijoc.2011.11002

Abstract

Oxidation of aliphatic and aromatic halides by N-oxide functionalities supported on 4- vinyl pyridine, (4-VP), grafted cellulose is reported in the present manuscript. Synthesis of graft copolymer of cellulose and poly 4-vinyl pyridine, poly(4-VP), has been carried out using ceric ions as redox initiator. Post-grafting treatment of CellO-g-poly (4-VP) with 30% H2O2 in acetic acid gives Cellulose-g-poly (4-VP) N-oxide, the polymeric supported oxidizing reagent. The polymeric support, CellO-g-poly (4-VP) N-oxide, has been used for oxidation reactions of different alkyl / aryl halide such as 1-bromo-3-methyl butane, 2-bromo propane,1-bromo heptane and benzyl chloride. The polymeric reagent was characterized by IR and thermo-gravimetric analysis. The oxidized products were characterized by FTIR and H1NMR spectral methods. The reagent was reused for the oxidation of a fresh alkyl / aryl halides and it was observed that the polymeric reagent oxidizes the compounds successfully but with little lower product yield.

Highlights

Preparation of chemically modified polymer surfaces with controllable structures is an area of current research, having both theoretical and practical interest [1]
Oxidation of aliphatic and aromatic halides by N-oxide functionalities supported on 4-vinyl pyridine, (4-VP), grafted cellulose is reported in the present manuscript
In the present work grafting onto cellulose is carried out in the presence of 4-VP, by chemical method using ceric ammonium nitrate (CAN) as redox initiator

Summary

Introduction

Preparation of chemically modified polymer surfaces with controllable structures is an area of current research, having both theoretical and practical interest [1]. The objective is to devise mild techniques of primary surface functionalization with a high degree of chemo- and topological selectivity. The primary functional groups on the surface should be capable of undergoing a variety of organic chemical transformations under mild conditions, enabling creation of novel secondary surface functionalities

Methods

Results

Conclusion