Abstract
The easily prepared bishomosecoheptaprismane ring system of 1 was converted to the tetracyclo[8.5.0.0 2,8.0 7,11]pentadeca-3,5,12,14-tetraene ring system of 10 using a photochemical decarbonylation/fragmentation reaction as the key step. The closely held face-to-face butadiene units in 10 undergo [4+4]cycloaddition under photochemical conditions and participate in domino Diels-Alder reactions with maleic anhydride and dicyanoacetylene. The maleic anhydride domino Diels-Alder adduct 18 was converted to the previously unreported hexacyclo[8.5.1.1 4,7.0 5,14.0 6,16.0 11,15.0 16,17]heptadecane ring system embodied in 19. A single crystal X-ray analysis of 20, one member of this new ring system, is reported and the results are compared with ab initio molecular orbital calculations.
Published Version
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