Directed lithiations: the effect of varying directing group orientation on competitive efficiencies for a series of tertiary amide, secondary amide, and alkoxide directed …

P Beak, ST Kerrick, DJ Gallagher

Index: Beak, Peter; Kerrick, Shawn T.; Gallagher, Donald J. Journal of the American Chemical Society, 1993 , vol. 115, # 23 p. 10628 - 10636

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Citation Number: 90

Abstract

Abstract: Significant differences for competitive efficiencies in directed ortho lithiations for single functional groups in three series, the secondary benzamides 1-4, the tertiary benzamides 5-1 1, and the benzylic alcohols 12-17, are reported. For both amide series the efficiencies increase as the oxygen and ortho hydrogen in the substrate are more coplanar with the aromatic ring; however, for the alcohol series the opposite order is observed. ...