Oxidative transformations using n ndibromoptoluene sulfonamide

Abstract

Oxidative transformations using N,N-Dibromo-p-toluene sulfonamide As a part of the Ph. D. work, we have carried out an investigation on the use of N,N-dibromo-p-toluene sulfonamide (TsNBr2) for various organic transformations such as bromination and oxidation reaction. The thesis contains six chapters which are summarized below. 1. Introduction 2. Regio- and stereo-selective synthesis of vicnal bromohydrins and alkoxybromides from olefin. 3. Oxidation of alcohol to corresponding carbonyl compounds. 4. Regeneration of carbonyl compound from the corresponding oxime. 5. Bromination of anilines 6. Oxidative dimerisation of thiols to disulfide CHAPTER I INTRODUCTION: Bromination and oxidation reactions are the important and widely used reactions in organic chemistry. Different brominated products are conveniently synthesized in the laboratory by using different types of brominating agents. Brominated products have very important biological properties such as antitumor, antibacterial, anti-fungal, antineoplastic, antiviral property and also used as intermediates for industrial manufacture of specialty chemicals, pharmaceuticals, and agro-chemicals. Numerous industrially valuable products such as flame retardant, herbicides, biocides and other new materials carry bromofunctionality. In this chapter, we have discussed about different types of bromo-compounds which are used for the bromination and oxidation reactions. CHAPTER II REGIO- AND STEREO-SELECTIVE SYNTHESIS OF VICNAL BROMOHYDRINS AND ALKOXYBROMIDES FROM OLEFIN. This chapter deals with the utilization of TsNBr2 for the bromohydrin and alkoxybromide The vicinal functionalization of olefin is a powerful synthetic tool for organic chemists. Particularly, selective introduction of two different functional groups, such as hydroxy or alkoxy is of great importance in organic as well as medicinal chemistry. Bromohydrins are synthesized by reacting an olefin with TsNBr2 in a mixture of acetonitrile and water in 4:1 ratio (Scheme 1).1 Scheme 1 The reaction was carried out...