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Friedel-Crafts acylation of alkenes with β,γ-unsaturated acid chlorides produces, among other products, cyclohexenones. The formation of cyclohexenones was rationalized by electrocyclization of intermediate aluminum trienolates: Faure, R.; Pommier, A.; Pons, J. M.; Rajzmann, M.; Santelli, M. Tetrahedron 1992, 48, 8419-8430.
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26
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4644241011
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ATPH is aluminum tris(2,6-diphenylphenoxide)
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ATPH is aluminum tris(2,6-diphenylphenoxide).
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28
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33845278128
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10744228872
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Aside from the stereochemical probe, it is hard to distinguish between the two mechanistic pathways because orbital interactions that favor Michael-type addition also enhance electrocyclization: Davies, I. W.; Marcoux, J.-F.; Kuethe, J. T.; Lankshear, M. D.; Taylor, J. D. O.; Tsou, N.; Dormer, P. G.; Hughes, D. L.; Houk, K. N.; Guner, V. J. Org. Chem. 2004, 69, 1298-1308.
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31
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4644241012
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note
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The same ratio of isomers was obtained when a sample of pure trans-15 was submitted to the cyclization conditions.
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33
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0000938909
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Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York
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Evans, D.A.1
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4644268338
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See, for example: (a) Paquette, L. A.; Barrett, J. H. J. Am. Chem. Soc. 1966, 88, 2590-2591. (b) Goldstein, M. J.; Dai, S.-H. J. Am. Chem. Soc. 1973, 95, 933-935.
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Paquette, L.A.1
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4644303245
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See, for example: (a) Paquette, L. A.; Barrett, J. H. J. Am. Chem. Soc. 1966, 88, 2590-2591. (b) Goldstein, M. J.; Dai, S.-H. J. Am. Chem. Soc. 1973, 95, 933-935.
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Goldstein, M.J.1
Dai, S.-H.2
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