Methylation of 2-methylstilbene with methyl-sulphinyl anion (MeSOCH2–) can be controlled to produce either the corresponding α- or α′-methylated stilbene: similar methylation of the more hindered 2,6-dimethyl-stilbene (3a) produced almost entirely the Z-form (4) of the α-methyl analogue, but the 2,2′,6,6′-tetramethylstilbene (3d) failed to react with MeSOCH2–.
B. G. James and G. Pattenden, J. Chem. Soc. D, 1971, 1015 DOI: 10.1039/C29710001015
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