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By E. Merck. Authorized translation by Henry Schenck ...

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Wisesser, Aldrichimica Acta 1989, 22(1), 17 (brief summary of Loschmidt’s work and biography). ¨ ckel, Zeitschrift fu¨r Physik 1931, 70, E. Hu 204–286. ¨ckel, Theoretical Principles of 7 E. Hu 8 9 10 11 12 Organic Chemistry, Elsevier, London, 1955, vol. 1. On Erich Hu¨ckel’s life, theory, and controversy: J. Berson, Chemical Creativity, Wiley-VCH, New York, 1999; Angew. Chem. Int. Ed. Engl. 1996, 35, 2750. J. C. Slater, Phys. Rev. 1930, 36, 57. B. Pullman, A. Pullman, Les The´ories Electroniques de la Chimie Organique, Masson, Paris, 1952.

Chim. Fr. 1865, 3(2), 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 100. a) C. Creutz, H. Taube, J. Am. Chem. Soc. 1969, 91, 3988; b) H. Taube, ElectronTransfer Reactions of Complex Ions in Solution, Academic Press, New York, 1970. a) I. L. , Vol. 1, 1967, p. 537. b) J. P. Snyder, Nonbenzenoid Aromatics, Academic Press, New York, 1969. P. Garratt, Aromaticity, Wiley, New York, 1986. I. Haller, J. Am. Chem. Soc. 1966, 88, 2070. E. E. van Tamelen, S. P. Papas, K. L. Kirk, J. Am. Chem. Soc. 1971, 93, 6092.

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.

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