Charge transfer induced osmylation of aromatic compounds

This thesis is divided into three chapters. The first chapter is a review of the published methods of inositol and conduritol syntheses with emphasis on the starting materials used. The routes from aromatics, carbohydrates and those involving Diels-Alder reactions are covered. The second chapter gives an in depth account of a new, one pot route to these cyclitols. This route employs stoichiometric chlorate salts and catalytic osmium tetroxide in a photochemically initiated cycle to oxidise simple aromatic substrates to inositols and conduritols. This new methodology is shown to be applicable to a number of substrates including alkyl benzenes and halobenzenes. It is shown that under dilute, room temperature conditions purely oxygenated cyclitols are obtained. With a greater concentration of reagents and reactants deoxy-chloro-inositols are obtained. The conduritol: inositol ratio of a given reaction is temperature dependant. On changing the stoichiometric oxidant to bromate deoxy-bromo-conduritols and inositols are accessible, the latter being used as a precursor for the synthesis of natural products pinitol and sequoyitol and other inositol methy1-ethers. The third chapter provides a formal description of experimental results and procedures.