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

doi:10.1039/b924791b

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

132 Downloads (Pure)

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.

Original language	English
Pages (from-to)	2319-2321
Number of pages	3
Journal	Chemical Communications (London)
Volume	46
Issue number	13
Early online date	20 Jan 2010
DOIs	https://doi.org/10.1039/b924791b
Publication status	Published - 7 Apr 2010

Keywords

ortho-zincation
benzyl methyl ether
chemistry

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10.1039/b924791b

Campbell-etal-CC-2010-Structual-elaboration-of-the-surprising-ortho-zincationAccepted author manuscript, 1.41 MB

Cite this

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title = "Structural elaboration of the surprising ortho-zincation of benzyl methyl ether",

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.",

keywords = "ortho-zincation, benzyl methyl ether, chemistry",

author = "Liam Balloch and Kennedy, \{Alan R.\} and Jan Klett and Mulvey, \{Robert E.\} and O'Hara, \{Charles T.\}",

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language = "English",

volume = "46",

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AU - Balloch, Liam

AU - Kennedy, Alan R.

AU - Klett, Jan

AU - Mulvey, Robert E.

AU - O'Hara, Charles T.

PY - 2010/4/7

Y1 - 2010/4/7

N2 - 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.

AB - 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.

KW - ortho-zincation

KW - benzyl methyl ether

KW - chemistry

UR - https://www.scopus.com/pages/publications/77949623079

U2 - 10.1039/b924791b

DO - 10.1039/b924791b

M3 - Article

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EP - 2321

JO - Chemical Communications (London)

JF - Chemical Communications (London)

IS - 13

ER -

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

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

Abstract

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

"INVERSE" COORDINATION: A NEW DESIGN CONCEPT IN SUPRAMOLECULAR INORGANIC CHEMISTRY

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x-ray diffractometer

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