Synthesis of bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) derivatives functionalised with two, four or eight hydroxyl groups

Short synthetic routes to a range of BEDT-TTF derivatives functionalised with two, four or eight hydroxyl groups are reported, of interest because of their potential for introducing hydrogen bonding between donor and anion into their radical cation salts. The cycloaddition of 1,3-dithiole-2,4,5-trithione with alkenes to construct 5,6-dihydro-1,3-dithiolo[4,5-b]1,4-dithiin-2-thiones is a key step, with homo- or hetero-coupling procedures and O-deprotection completing the syntheses. The first synthesis of a single diastereomer of tetrakis(hydroxymethyl)BEDT-TTF, the cis, trans product, was achieved by careful choice of O-protecting groups to facilitate separation of homo- and hetero-coupled products. Cyclisation of the trithione with enantiopure 1R,2R,5R,6R-bis(O,O-isopropylidene)hex-3-ene-1,2,5,6-tetrol (from D-mannitol) gave two separable diastereomeric thiones, which can be transformed to enantiomeric BEDT-TTF derivatives with four or eight hydroxyl groups

National Bureau of Standards Reports

Report discussing the literature on the oxidation of polycyclic, aromatic hydrocarbons. Information has been assembled on (1) the oxidants effective in the oxidation of such hydrocarbons, (2) the relative reactivity of the hydrocarbons, (3) the conditions under which oxidation proceeds, (4) the chemical mechanisms involved when such oxidations occur, and (5) the products formed

National Bureau of Standards Reports

Report presenting of survey of the literature on the infrared spectroscopy of carbohydrates in order to assemble and systematize information in this field. Discusses principles and instrumentation, sampling techniques, comparison of samples, and the interpretation of the spectra. In addition, examples are discussed of the use of infrared spectra for qualitative and quantitative purposes and in the determination of structure. Special techniques are briefly described

Advances in Carbohydrate Chemistry and Biochemistry

xii.440 Hal.;ill.;23 c