Polyfluoroarenes. Part IX. Decafluorotolan: synthesis, properties, and use as an organometallic ligand
- 1 January 1967
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in J. Chem. Soc. A
- p. 747-753
- https://doi.org/10.1039/j19670000747
Abstract
Di-iodoacetylene and pentafluorophenylmagnesium bromide give decafluorotolan (C6F5·C⋮C·C6F5) in good yield. The triple bond in the tolan undergoes ready catalytic hydrogenation, addition of bromine, and oxidative cleavage, but is relatively unreactive towards hydration, iodination, and carbonylation. Decafluorotolan reacts with methoxide ion in the 4- and 4′-positions, and gives a good yield of tetrakispentafluorophenylthiophen when it is heated with sulphur. Reaction of the tolan with cobalt octacarbonyl yields a complex Co2(CO)6(C6F5·C⋮C·C6F 5), shown by its chemical and spectroscopic properties to be similar in structure to its hydrocarbon analogue; octafluoro-4,4′-dimethoxytolan behaves similarly. Tetrakispentafluorophenylcyclopentadienone (perfluorotetracyclone) is obtained when a solution of the cobalt carbonyl complex of decafluorotolan is heated. Reaction of decafluorotolan with iron penta- or dodeca-carbonyl yields a complex Fe2(CO)6(C6F5·C⋮C·C6F 5)2, together with perfluorotetracyclone.Keywords
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