The first centrohexaindane bearing twelve functional groups at its outer molecular periphery and related lower veratrole-derived centropolyindanes

Harig M, Kuck D. The first centrohexaindane bearing twelve functional groups at its outer molecular periphery and related lower veratrole-derived centropolyindanes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2006;(7):1647-1655.The first T-d-symmetrical derivative of centrohexaindane bearing twelve functional groups has been synthesized. Six pairs of methoxy groups, each of which belong to six veratrole units fused to the topologically nonplanar (K-5) core, point outwards from the molecular center into the six directions of the Cartesian space. The synthesis of this first dodeca-substituted centrohexaindane was achieved along the "propellane route" established previously for the parent centrohexaindane, but the electron-rich character of some of the intermediates was found to require considerably modified methodology. Two hexamethoxy-substituted centrotriindanes, representing lower congeners of the title compound and bearing three veratrole units, were also synthesized. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006