Collect. Czech. Chem. Commun. 1981, 46, 1474-1485
https://doi.org/10.1135/cccc19811474

Cycloheptatriene dimers: New precursors of diamantane

František Turečeka, Vladimír Hanuša, Petr Sedmerab, Helena Antropiusováa and Karel Macha

a The J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague 2
b Institute of Microbiology, Czechoslovak Academy of Sciences, 142 20 Prague 4

Abstract

Dimerization of cycloheptatriene, catalyzed by titanium complexes, afforded pentacyclo[8.4.0.03,7.04,14.06,11]tetradeca-8,12-diene (I) (10%) and pentacyclo[7.5.0.02,8.05,14.07,11]tetradeca-3,12-diene (II) (90%). Structure of both dimers and their derivatives was determined by means of 1H NMR, 13C NMR and mass spectra. On heating, the diene II was converted into the more stable isomer I. On hydrogenation and further catalytic isomerization, both I and II gave diamantane in high yield.