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Structural elaboration of the surprising ortho-zincation of benzylmethylether

Mulvey, R.E. and Kennedy, A.R. and Klett, J. and O'Hara, C.T. (2010) Structural elaboration of the surprising ortho-zincation of benzylmethylether. Chemical Communications (London), 46. pp. 2319-2321. ISSN 0009-241X

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Abstract

Breaking with convention, the reaction of the sodium zincate, [(TMEDA)Na(μ-TMP)(μ-tBu)Zn(tBu)] with benzyl methyl ether (PhCH2OMe) produces exclusively an ortho-zincated intermediate [(TMEDA)Na(μ-TMP)(μ-C6H4CH2OMe)Zn(tBu)] instead of the expected 'thermodynamic' α-metallated product.