Ethoxyvinyllithium-HMPA. Surprising Regiochemistry in Aromatic Metalation

M Shimano, AI Meyers

Index: Shimano, Masanao; Meyers Journal of the American Chemical Society, 1994 , vol. 116, # 23 p. 10815 - 10816

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Citation Number: 40

Abstract

The large volume of data on aromatic metalation in the presence of various ortho-activating groups has provided synthetic chemistry with many useful transformations.'However, in virtually every instance, the bases used to effect ortho metalation have been those derived from alkyl-and aryllithium compounds. It was, therefore, rather unexpected to find that alkoxyvinyllithium reagents, shown earlier2, 3 to be mainly nucleophiles for" umpolung" ...