Stereomanipulation of (η5-1-arylcyclohexadienyl)iron complexes

Christopher E. Anson; Andrei V. Malkov; Caroline Roe; Elizabeth J. Sandoe; G. Richard Stephenson

doi:10.1002/ejoc.200700919

Stereomanipulation of (η5-1-arylcyclohexadienyl)iron complexes

Christopher E. Anson, Andrei V. Malkov, Caroline Roe, Elizabeth J. Sandoe, G. Richard Stephenson

Chemistry of Materials and Catalysis

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Abstract

A crystallographic investigation comparing five 1-aryl-substituted tricarbonyl[(1–5-?)-cyclohexadienyl]iron(1+) salts demonstrates that introducing additional electron density on the aromatic ring increases p overlap between the arene and the cyclohexadienyl ligand, thus flattening the structures sufficiently to make available a conformation in which nucleophiles can approach the site of substitution, despite the steric blockade of o-benzyl substituents.

Original language	English
Pages (from-to)	196-213
Number of pages	18
Journal	European Journal of Organic Chemistry
Volume	2008
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.200700919
Publication status	Published - Jan 2008

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10.1002/ejoc.200700919

15 Citations (Scopus)
1 Article

Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent
Stephenson, G., Palotai, I. M., Thomas, S. & Tinkl, M., Apr 2013, In: European Journal of Organic Chemistry. 2013, 10, p. 1895–1901 7 p.
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title = "Stereomanipulation of (η5-1-arylcyclohexadienyl)iron complexes",

abstract = "A crystallographic investigation comparing five 1-aryl-substituted tricarbonyl[(1–5-?)-cyclohexadienyl]iron(1+) salts demonstrates that introducing additional electron density on the aromatic ring increases p overlap between the arene and the cyclohexadienyl ligand, thus flattening the structures sufficiently to make available a conformation in which nucleophiles can approach the site of substitution, despite the steric blockade of o-benzyl substituents.",

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pages = "196--213",

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AU - Anson, Christopher E.

AU - Malkov, Andrei V.

AU - Roe, Caroline

AU - Sandoe, Elizabeth J.

AU - Stephenson, G. Richard

PY - 2008/1

Y1 - 2008/1

N2 - A crystallographic investigation comparing five 1-aryl-substituted tricarbonyl[(1–5-?)-cyclohexadienyl]iron(1+) salts demonstrates that introducing additional electron density on the aromatic ring increases p overlap between the arene and the cyclohexadienyl ligand, thus flattening the structures sufficiently to make available a conformation in which nucleophiles can approach the site of substitution, despite the steric blockade of o-benzyl substituents.

AB - A crystallographic investigation comparing five 1-aryl-substituted tricarbonyl[(1–5-?)-cyclohexadienyl]iron(1+) salts demonstrates that introducing additional electron density on the aromatic ring increases p overlap between the arene and the cyclohexadienyl ligand, thus flattening the structures sufficiently to make available a conformation in which nucleophiles can approach the site of substitution, despite the steric blockade of o-benzyl substituents.

U2 - 10.1002/ejoc.200700919

DO - 10.1002/ejoc.200700919

M3 - Article

VL - 2008

SP - 196

EP - 213

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 1

ER -

Stereomanipulation of (η5-1-arylcyclohexadienyl)iron complexes

Abstract

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Research output

Synthetic studies for the 1,3-iterative organoiron approach to the synthesis of siculinine: efficient arylation using a diarylcuprate reagent

Cite this