Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 6 (June 2008)

organic compounds

su3020 scheme

Acta Cryst. (2008). C64, o319-o321 [ doi:10.1107/S0108270108011876 ]

rac-9-Ethyl-12a-hydroxytetradecahydrotriphenylene-1,5(2H,4bH)-dione: stabilization of a new isomer of a functionalized perhydrotriphenylene through a tandem Michael addition-aldol reaction

L. A. García, S. Bernès and C. Anaya de Parrodi

Abstract: The title compound, C₂₀H₃₀O₃, is a new functionalized perhydrotriphenylene derivative formed via a tandem Michael addition-aldol reaction. The structural study reveals that the system of fused rings approximates a C₂ point symmetry, with trans-cis-cis ring junctions, while highly symmetric all-trans perhydrotriphenylene, previously characterized, approximates a D₃ symmetry. The perhydrotriphenylene nucleus of the title compound corresponds to the third stable stereoisomer isolated for this polycyclic system. Considering that the C_s isomer was obtained recently through a similar tandem reaction, a general strategy is proposed which may help to obtain other stable stereoisomers of perhydrotriphenylene.

Formula: C₂₀H₃₀O₃