The effect of an alkoxy group on the kinetic and thermodynamic acidity of benzene and toluene
M Schlosser, P Maccaroni, E Marzi
Index: Schlosser, Manfred; Maccaroni, Paola; Marzi, Elena Tetrahedron, 1998 , vol. 54, # 12 p. 2763 - 2770
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Citation Number: 32
Abstract
2-, 3-and 4-Methoxytoluene can be selectively metalated at an O-adjacent ortho position when butyllithium or tert-butyllithium in the presence of sodium (potassium) tert-butoxide or N, N, N′, N ″, N ″-pentamethyldiethylenetriamine are employed as reagents. In contrast, lithium diisopropylamide or lithium 2, 2, 6, 6-tetramethylpiperidide deprotonate the benzylic α-position of 2-and 3-methoxy-toluene exclusively and of 4-methoxytoluene preferentially. ...
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