FROM PAGODANES TO DODECAHEDRANES - SEARCH FOR A SERVICEABLE ACCESS TO THE PARENT (C20H20) HYDROCARBON

摘要

By taking advantage of the novel S(N)2 pagodane --> dodecahedrane routes a preparatively potent access to the parent pentagonal dodecahedrane (2) was explored. The one-pot catalytic procedure (Pd/C/H-2) starting from an eightfold functionalized secopagodane (14, C20H12Br6 (CO2 CH3)(2)) excells in shortness but, rather erratic (33-53%), falls out of the competition. The longer route via 1,6-dicarboxyl/dibromo dodecahedranes (35, 22) turned out as first choice with a total yield of 74-76% based on the common pagodane precursor (13). (C) 1997 Elsevier Science Ltd. [References: 79]