The first crystallographic evidence for the structures of ortho-lithiated aromatic tertiary amides

Jonathan Clayden; Robert P. Davies; Mark A. Hendy; Ronald Snaith; Andrew E H Wheatley

doi:10.1002/1521-3773(20010401)40:7<1238::AID-ANIE1238>3.0.CO;2-G

The first crystallographic evidence for the structures of ortho-lithiated aromatic tertiary amides

Jonathan Clayden^*, Robert P. Davies, Mark A. Hendy, Ronald Snaith, Andrew E H Wheatley

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

46 Citations (Scopus)

Abstract

Despite the near-perpendicular arrangement of the amide group and aromatic ring in many tertiary aromatic amides, ortho-lithiation is still a very straightforward process. The first X-ray crystal structures of ortho-lithiated amides reveal why: the angle of twist is lessened to some degree, and the lithium ion lies far from the plane of the aromatic ring, with stabilization of the strained structure being achieved by dimerization (see scheme).

Original language	English
Pages (from-to)	1238-1240
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	7
Early online date	27 Mar 2001
DOIs	https://doi.org/10.1002/1521-3773(20010401)40:7<1238::AID-ANIE1238>3.0.CO;2-G
Publication status	Published - 1 Apr 2001

Keywords

Amides
Lithiation
Ortho-metalation
Solid-state structures

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abstract = "Despite the near-perpendicular arrangement of the amide group and aromatic ring in many tertiary aromatic amides, ortho-lithiation is still a very straightforward process. The first X-ray crystal structures of ortho-lithiated amides reveal why: the angle of twist is lessened to some degree, and the lithium ion lies far from the plane of the aromatic ring, with stabilization of the strained structure being achieved by dimerization (see scheme).",

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T1 - The first crystallographic evidence for the structures of ortho-lithiated aromatic tertiary amides

AU - Clayden, Jonathan

AU - Davies, Robert P.

AU - Hendy, Mark A.

AU - Snaith, Ronald

AU - Wheatley, Andrew E H

PY - 2001/4/1

Y1 - 2001/4/1

N2 - Despite the near-perpendicular arrangement of the amide group and aromatic ring in many tertiary aromatic amides, ortho-lithiation is still a very straightforward process. The first X-ray crystal structures of ortho-lithiated amides reveal why: the angle of twist is lessened to some degree, and the lithium ion lies far from the plane of the aromatic ring, with stabilization of the strained structure being achieved by dimerization (see scheme).

AB - Despite the near-perpendicular arrangement of the amide group and aromatic ring in many tertiary aromatic amides, ortho-lithiation is still a very straightforward process. The first X-ray crystal structures of ortho-lithiated amides reveal why: the angle of twist is lessened to some degree, and the lithium ion lies far from the plane of the aromatic ring, with stabilization of the strained structure being achieved by dimerization (see scheme).

KW - Amides

KW - Lithiation

KW - Ortho-metalation

KW - Solid-state structures

UR - http://www.scopus.com/inward/record.url?scp=0035794902&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20010401)40:7<1238::AID-ANIE1238>3.0.CO;2-G

DO - 10.1002/1521-3773(20010401)40:7<1238::AID-ANIE1238>3.0.CO;2-G

M3 - Article (Academic Journal)

AN - SCOPUS:0035794902

SN - 1433-7851

VL - 40

SP - 1238

EP - 1240

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 7

ER -

The first crystallographic evidence for the structures of ortho-lithiated aromatic tertiary amides

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Keywords

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