Synthesis and properties of polycyclic quinones condensed with 1,6-methano[10]annulene

Two types of polycyclic quinones condensed with 1,6-methano[10]annulenes as type A: 1,6-methanonaphtho[2,3-c][10]annulene-7,12-dione 5a, and type B: 1,6-methanonaphtho[2,3-c][10]annulene-5,14-dione 18, bis(1,6-methano[10]annuleno[3,4-b; 3,4-g])anthracene-10,21-dione 20, 1,6-methanoanthraceno[2,3-c][10]annulene-5,16-dione 22, 1,6-methanotetraceno[2,3-c][10]annulene-6,17-dione 23, and 1,6-methano phenanthreno[2,3-c][10]annulene-5,6-dione 24 have been synthesized. The acene derivative 6 corresponding to that of 5a was synthesized by the reduction of quinone 5a. The physical, spectral, and chemical properties of these new compounds have been investigated.