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Charge transfer induced osmylation of aromatic compounds

Williams, Alvin Scott; (1995) Charge transfer induced osmylation of aromatic compounds. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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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.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: Charge transfer induced osmylation of aromatic compounds
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Thesis digitised by ProQuest.
Keywords: Pure sciences; Aromatic compounds; Charge transfer; Osmylation
URI: https://discovery.ucl.ac.uk/id/eprint/10104238
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