Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities

David R. Armstrong; Pablo Garcia-Álvarez; Alan R. Kennedy; Robert E. Mulvey; John A. Parkinson

doi:10.1002/anie.201000539

Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities

David R. Armstrong, Pablo Garcia-Álvarez, Alan R. Kennedy, Robert E. Mulvey, John A. Parkinson

Pure And Applied Chemistry

Research output: Contribution to journal › Article

65 Citations (Scopus)

237 Downloads (Pure)

Abstract

A neutral dimeric molecule in crystal form, the diisopropylamido turbo-Grignard reagent "(iPr₂N)MgCl⋅LiCl" (see structure; blue N, red O, green Mg, yellow Cl, black C) separates into several charged ate species in dynamic exchange with each other in THF solution as determined by a combination of EXSY and DOSY NMR studies.

Original language	English
Pages (from-to)	3185–3188
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	49
Issue number	18
Early online date	29 Mar 2010
DOIs	https://doi.org/10.1002/anie.201000539
Publication status	Published - 19 Apr 2010

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Keywords

amides
grignard reagents
metalation
structure elucidation
DOSY NMR spectroscopy

Cite this

Armstrong, D. R., Garcia-Álvarez, P., Kennedy, A. R., Mulvey, R. E., & Parkinson, J. A. (2010). Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities. Angewandte Chemie International Edition , 49(18), 3185–3188. https://doi.org/10.1002/anie.201000539

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title = "Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities",

abstract = "A neutral dimeric molecule in crystal form, the diisopropylamido turbo-Grignard reagent {"}(iPr2N)MgCl⋅LiCl{"} (see structure; blue N, red O, green Mg, yellow Cl, black C) separates into several charged ate species in dynamic exchange with each other in THF solution as determined by a combination of EXSY and DOSY NMR studies.",

keywords = "amides, grignard reagents, metalation, structure elucidation, DOSY NMR spectroscopy",

author = "Armstrong, {David R.} and Pablo Garcia-{\'A}lvarez and Kennedy, {Alan R.} and Mulvey, {Robert E.} and Parkinson, {John A.}",

note = "This is the peer reviewed version of the following article: Armstrong, DR, Garcia-{\'A}lvarez, P, Kennedy, AR, Mulvey, RE & Parkinson, JA 2010, 'Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities' Angewandte Chemie International Edition , vol 49, no. 18, pp. 3185–3188, which has been published in final form at https://doi.org/10.1002/anie.201000539. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.",

year = "2010",

month = "4",

day = "19",

doi = "10.1002/anie.201000539",

language = "English",

volume = "49",

pages = "3185–3188",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

number = "18",

}

TY - JOUR

T1 - Diisopropylamide and TMP turbo-grignard reagents

T2 - a structural rationale for their contrasting reactivities

AU - Armstrong, David R.

AU - Garcia-Álvarez, Pablo

AU - Kennedy, Alan R.

AU - Mulvey, Robert E.

AU - Parkinson, John A.

N1 - This is the peer reviewed version of the following article: Armstrong, DR, Garcia-Álvarez, P, Kennedy, AR, Mulvey, RE & Parkinson, JA 2010, 'Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities' Angewandte Chemie International Edition , vol 49, no. 18, pp. 3185–3188, which has been published in final form at https://doi.org/10.1002/anie.201000539. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

PY - 2010/4/19

Y1 - 2010/4/19

N2 - A neutral dimeric molecule in crystal form, the diisopropylamido turbo-Grignard reagent "(iPr2N)MgCl⋅LiCl" (see structure; blue N, red O, green Mg, yellow Cl, black C) separates into several charged ate species in dynamic exchange with each other in THF solution as determined by a combination of EXSY and DOSY NMR studies.

AB - A neutral dimeric molecule in crystal form, the diisopropylamido turbo-Grignard reagent "(iPr2N)MgCl⋅LiCl" (see structure; blue N, red O, green Mg, yellow Cl, black C) separates into several charged ate species in dynamic exchange with each other in THF solution as determined by a combination of EXSY and DOSY NMR studies.

KW - amides

KW - grignard reagents

KW - metalation

KW - structure elucidation

KW - DOSY NMR spectroscopy

UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

U2 - 10.1002/anie.201000539

DO - 10.1002/anie.201000539

M3 - Article

VL - 49

SP - 3185

EP - 3188

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 18

ER -

Access to Document

10.1002/anie.201000539

Armstrong-etal-ACIE2010-Diisopropylamide-and-TMP-turbo-grignard-reagentsAccepted author manuscript, 5.04 MB
strathprints027619.pdfAccepted author manuscript, 5.36 MB

http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

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Diisopropylamide and TMP turbo-grignard reagents: a structural rationale for their contrasting reactivities

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Keywords

Cite this

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