The oxazoline-benzyne route to 1, 2, 3-trisubstituted benzenes. Tandem addition of organolithiums, organocuprates, and. alpha.-lithionitriles to benzynes

PD Pansegrau, WF Rieker…

Index: Pansegrau,P.D.; Rieker,W.F.; Meyers,A.I. Journal of the American Chemical Society, 1988 ,  vol. 110, p. 7178            

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Citation Number: 70

Abstract

Abstract: The generation of a benzyne intermediate 4 via ortho lithiation of readily available (m-ch1orophenyl) oxazoline 1 gives rise to a variety of polysubstituted benzene derivatives. The key property of 4 is its ability to form benzyne at temperatures between-10 and 0 OC, which allows a variety of nucleophiles to be placed in solution. As the ortho lithio intermediate loses lithium chloride to form the benzyne, mostly clean regiospecific ...