The dianion of α-phenylsulphinyl cyclopenta-none can be alkylated exclusively at the C-5 position; the resultant 5-alkyl-2-phenylsulphinyl cyclopentanone upon pyrolysis yields 5-alkyl-Δ2-cyclopentenone with complete exclusion of the more stable 2-alkyl-Δ2-cyclopentenone: similary α-phenylsulphinyl cyclohexanone provides access to 6-alkyl-Δ2-cyclohexenones.
P. A. Grieco and C. S. Pogonowski, J. Chem. Soc., Chem. Commun., 1975, 72 DOI: 10.1039/C39750000072
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