Buckybowls. 2. Toward the Total Synthesis of Buckminsterfullerene (C_(60)): Benz[5,6]-as-indaceno-[3,2,1,8,7-mnopqr]indeno[4,3,2,1-cdef]chrysene

摘要

The discovery of buckminsterfullerene (C_(60)) and related carbon cages has generated enormous interest, and the availability of C_(60) in macroscopic amounts has spawned a considerable amount of research. However, the production of C_(60) by the vaporization of carbon rods notwithstanding, the total synthesis of C_(60) provides an exciting but formidable challenge to organic chemists. Clearly, the most critical step in such a synthesis will be the production of intermediates that possess significant degrees of curvature, and one approach, suggested by several groups, is the dimerization of two C_(60)H_(12) halves. We now report the first synthesis of a C_(60)H_(12) hydrocarbon (benz-[5,6]-as-indaceno[3,2,1,8,7-mnopqr]indeno[4,3,2,1-cdef]chrysene)-that represents precisely half of the C_(60) carbon framework, albeit as enantiomeric pairs.