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

Research output: Contribution to journalArticle

63 Citations (Scopus)

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.
LanguageEnglish
Pages3185–3188
Number of pages4
JournalAngewandte Chemie International Edition
Volume49
Issue number18
Early online date29 Mar 2010
DOIs
Publication statusPublished - 19 Apr 2010

Fingerprint

Thymidine Monophosphate
Ion exchange
Nuclear magnetic resonance
Crystals
Molecules

Keywords

  • amides
  • grignard reagents
  • metalation
  • structure elucidation
  • DOSY NMR spectroscopy

Cite this

@article{4995addad9894d29bf37497d603a9b44,
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",

}

Diisopropylamide and TMP turbo-grignard reagents : a structural rationale for their contrasting reactivities. / Armstrong, David R.; Garcia-Álvarez, Pablo; Kennedy, Alan R.; Mulvey, Robert E.; Parkinson, John A.

In: Angewandte Chemie International Edition , Vol. 49, No. 18, 19.04.2010, p. 3185–3188.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Diisopropylamide and TMP turbo-grignard reagents

T2 - Angewandte Chemie International Edition

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 -