“LiZn(TMP)3”, a zincate or a turbo-lithium amide reagent?: DOSY NMR spectroscopic evidence

Pablo Garcia-Alvarez; Robert Mulvey; John Parkinson

doi:10.1002/anie.201104297

“LiZn(TMP)₃”, a zincate or a turbo-lithium amide reagent? DOSY NMR spectroscopic evidence

Pablo Garcia-Alvarez, Robert Mulvey, John Parkinson

Pure And Applied Chemistry

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

67 Citations (Scopus)

Abstract

DOSY NMR studies (see picture; TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N′,N′-tetramethylethylenediamine) reveal the true nature of the synthetically useful basic mixture formed by reacting three equivalents of LiTMP with one of (TMEDA)⋅ZnCl2 in THF. Surprisingly, Zn(TMP)2 is just a spectator of the mutual interactions shown between LiTMP and the LiCl coproduct released from the transmetalation/“salt elimination” reaction.

Original language	English
Pages (from-to)	9668-9671
Number of pages	4
Journal	Angewandte Chemie
Volume	50
Issue number	41
DOIs	https://doi.org/10.1002/anie.201104297
Publication status	Published - 4 Oct 2011

Keywords

turbo-lithium amide reagent
zincate
spectroscopy
structure elucidation
lithium chloride
lithium zincates

Access to Document

10.1002/anie.201104297

EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)
Mulvey, R. & Kennedy, A.
EPSRC (Engineering and Physical Sciences Research Council)
1/10/08 → 31/03/12
Project: Research

Cite this

@article{f03d1ff4c4c5400c8f4c556fda6a7f59,

title = "“LiZn(TMP)3”, a zincate or a turbo-lithium amide reagent?: DOSY NMR spectroscopic evidence",

abstract = "DOSY NMR studies (see picture; TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N′,N′-tetramethylethylenediamine) reveal the true nature of the synthetically useful basic mixture formed by reacting three equivalents of LiTMP with one of (TMEDA)⋅ZnCl2 in THF. Surprisingly, Zn(TMP)2 is just a spectator of the mutual interactions shown between LiTMP and the LiCl coproduct released from the transmetalation/“salt elimination” reaction.",

keywords = "turbo-lithium amide reagent, zincate, spectroscopy, structure elucidation, lithium chloride, lithium zincates",

author = "Pablo Garcia-Alvarez and Robert Mulvey and John Parkinson",

year = "2011",

month = oct,

day = "4",

doi = "10.1002/anie.201104297",

language = "English",

volume = "50",

pages = "9668--9671",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

number = "41",

}

TY - JOUR

T1 - “LiZn(TMP)3”, a zincate or a turbo-lithium amide reagent?

T2 - DOSY NMR spectroscopic evidence

AU - Garcia-Alvarez, Pablo

AU - Mulvey, Robert

AU - Parkinson, John

PY - 2011/10/4

Y1 - 2011/10/4

N2 - DOSY NMR studies (see picture; TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N′,N′-tetramethylethylenediamine) reveal the true nature of the synthetically useful basic mixture formed by reacting three equivalents of LiTMP with one of (TMEDA)⋅ZnCl2 in THF. Surprisingly, Zn(TMP)2 is just a spectator of the mutual interactions shown between LiTMP and the LiCl coproduct released from the transmetalation/“salt elimination” reaction.

AB - DOSY NMR studies (see picture; TMP=2,2,6,6-tetramethylpiperidide; TMEDA=N,N,N′,N′-tetramethylethylenediamine) reveal the true nature of the synthetically useful basic mixture formed by reacting three equivalents of LiTMP with one of (TMEDA)⋅ZnCl2 in THF. Surprisingly, Zn(TMP)2 is just a spectator of the mutual interactions shown between LiTMP and the LiCl coproduct released from the transmetalation/“salt elimination” reaction.

KW - turbo-lithium amide reagent

KW - zincate

KW - spectroscopy

KW - structure elucidation

KW - lithium chloride

KW - lithium zincates

U2 - 10.1002/anie.201104297

DO - 10.1002/anie.201104297

M3 - Article

VL - 50

SP - 9668

EP - 9671

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 41

ER -

“LiZn(TMP)3”, a zincate or a turbo-lithium amide reagent? DOSY NMR spectroscopic evidence

Abstract

Keywords

Access to Document

Fingerprint

Projects

EXPLOITING SYNTHETIC AND STRUCTURAL SYNERGISM IN ALKALI-METAL-MEDIATED ORGANOTRANSITIONMETALLATION (AMMO)

Cite this

“LiZn(TMP)₃”, a zincate or a turbo-lithium amide reagent? DOSY NMR spectroscopic evidence