Collect. Czech. Chem. Commun. 1989, 54, 3260-3266

The Bayer-Villiger oxidation of diamantanone and the structure of 11-oxo-10-oxapentacyclo[7,4,1,14,13,02,7,06,12]-pentadecane

Jan Ondráčeka, Josef Jankůb, Jiří Novotnýa, Luděk Vodičkab, László Csordásc and Bohumil Kratochvíla

a Department of Solid State Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czechoslovakia
b Laboratory of Synthetic Fuels, Prague Institute of Chemical Technology, 166 28 Pragur 6, Czechoslovakia
c Laboratory of Surface and Interface Physics, Eotvos University, 1088 Budapest, Hungary


The studied substance was prepared by the Bayer-Villiger oxidation of diamantanone and identified by 1H and 13C NMR spectroscopy. The structure of the compound was solved by direct methods and refined to the value R = 0.052 for 845 observed reflections (I > 1.96σ(I)). The substance crystallizes in the orthorhombic space group Pnnm; a = 23.595(4), b = 10.284(2), c = 6.676(1) Å. The unit cell of the crystal structure of 11-oxo-10-oxapentacyclo[7,4,1,14,13,02,7,06,12]pentadecane contains four ordered and two disordered molecules. The disordered molecule is described by averaging the image of the ordered molecule and its inverse image. Thus, the unit cell contains 6 formula units (part of the atoms have fractional occupation factors) even though the multiplicity of the general position in the Pnnm group is 8.