Structural elaboration of the surprising ortho-zincation of benzyl methyl ether

Balloch, Liam and Kennedy, Alan R. and Klett, Jan and Mulvey, Robert E. and O'Hara, Charles T. (2010) Structural elaboration of the surprising ortho-zincation of benzyl methyl ether. Chemical Communications (London), 46 (13). 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.