Structural elaboration of the surprising ortho-zincation of benzyl methyl ether†,10.1039/B924791B

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

Liam Balloch,Alan R. Kennedy,Jan Klett,Robert E. Mulvey,Charles T. O’Hara

Chemical Communications Pub Date : 01/20/2010 00:00:00 , DOI:10.1039/B924791B

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.