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9. Aldol trimerization of 6-chloro-5-acephenanthrenone (39) to form a tris-annulated benzene. This behavior contrasts sharply with that of the closely related 6-chloro-4-acephenanthrenone (36) in Figure 7. 29 30 1 The Synthesis of Tris-Annulated Benzenes by Aldol Trimerization of Cyclic Ketones The only exception that we have encountered so far to predictions based on this analysis is the aldol trimerization of a-tetralone (38). At the level of theory used above (pBP/DN**// AM1), the most stable aldol dimer is found to be the (E )-a,b-unsaturated isomer, which, according to our hypothesis, should condense further and cyclize to the tris-annulated benzene product.