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Centrohexaindanes Bearing Methyl Groups in Their Molecular Propellane Cavities

Kuck D., Hackfort T., Neumann B., Stammler H.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

875-892

The syntheses of two new centrohexaindane derivatives bearing methyl groups in their molecular propellane-type cavities are described. These new topologically non-planar hydrocarbons, 1,8-dimethylcentrohexaindane 6 and 1,4,8,28-tetramethylcentrohexaindane 7 were obtained from suitable 1,3-indanediones following the shortest aufbau strategy, the propellane route, representing a six-step access to these unusually highly condensed polycyclic hydrocarbons. X-ray single crystal structure analysis of 6 revealed that the presence of the two methyl groups in the cavities of the centrohexaindane framework does not give rise to significant distortion of the Td-symmetrical molecular skeleton; however, their efficient hiding within two of the four equivalent cavities allows for strong intermolecular disorder in the crystal.

Voltammetric study of the Reduction of Triptindanones in N,N-Dimethylformamide

Jaworski J., Kuck D.

Polish Journal of Chemistry

2004

Vol. 78 / nr 9

1597-1604

The mechanism of electroreduction of 9-triptindanone (1), 9,10-triptindanedione (2), and 9,10,11-triptindanetrione (3) was studied by use of the cyclic voltammetric method. All carbonyl groups were reduced giving one, two, and three one-electron cathodic peaks for 1, 2, and 3, respectively and the corresponding oxidation peaks. The first electron transfer is reversible and the radical anions formed are stable. Additional small peaks for 2 and 3 were discussed in terms of an adsorption of reactants and intermediates and their reactions with the participation of supporting electrolyte cations as well as the residual water.