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Structural tracking of the potassium-mediated magnesiation of anisole

Clegg, W. and Conway, B. and Garcia-Alvarez, P. and Kennedy, A.R. and Mulvey, R.E. and Russo, L. and Sassmannshausen, J. and Tuttle, Tell (2009) Structural tracking of the potassium-mediated magnesiation of anisole. Chemistry - A European Journal, 15 (41). pp. 10702-10706. ISSN 0947-6539

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Abstract

The potassium-mediated magnesiation of anisole has been monitored by a combination of X-ray crystallographic and NMR spectroscopic studies. Departing from a heteroleptic alkyl-amido base and anisole, the reaction first stops at an ortho-magnesiated anisole intermediate, but the final destination is an ortho-magnesiated anisole complex with reincorporation of the amine ligand and elimination of alkane (see picture).