Synthesis and reactivity of η<sup>4</sup>-diene-Fe(CO)<inf>3</inf> complexes from exo-2-oxazolidinone dienes. A facile generation of stable conjugated enol-enamido species

Fernando Ortega-Jiménez, Adriana Benavides, Francisco Delgado, Hugo A. Jiménez-Vázquez, Joaquín Tamariz

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Abstract

A synthesis of new η4 -diene-Fe(CO)3 complexes derived from the novel exo-2-oxazolidinone dienes is described. These complexes were prepared by thermal complexation of the substituted dienes with diiron nonacarbonyl to afford the corresponding complexes as crystal solids. The X-ray single-crystal structure analysis revealed characteristic structural properties for diene-iron complexes, showing that in the conformation of the distorted trigonal-pyramidal geometry two of the carbonyl groups point out from the metal toward the vertex C4 and C5 atoms of the heterocycle. Unsuccessful functionalization of the diene moiety by acylation or alkylation of the allylic position indicated the strong stability of these dienes. This stability facilitated the generation of stable and unprecedented conjugated enamine-enol ester- and enamido-enol-Fe(CO)3 complexes, by either kinetic or themodynamic control of the reaction conditions. © 2009 American Chemical Society.
Original languageAmerican English
Pages (from-to)149-159
Number of pages133
JournalOrganometallics
DOIs
StatePublished - 11 Jan 2010

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Oxazolidinones
dienes
Carbon Monoxide
reactivity
Point groups
Acylation
Alkylation
synthesis
Complexation
Conformations
Structural properties
Esters
Iron
Hot Temperature
Crystal structure
Metals
X-Rays
Single crystals
X rays
Atoms

Cite this

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title = "Synthesis and reactivity of η4-diene-Fe(CO)3 complexes from exo-2-oxazolidinone dienes. A facile generation of stable conjugated enol-enamido species",
abstract = "A synthesis of new η4 -diene-Fe(CO)3 complexes derived from the novel exo-2-oxazolidinone dienes is described. These complexes were prepared by thermal complexation of the substituted dienes with diiron nonacarbonyl to afford the corresponding complexes as crystal solids. The X-ray single-crystal structure analysis revealed characteristic structural properties for diene-iron complexes, showing that in the conformation of the distorted trigonal-pyramidal geometry two of the carbonyl groups point out from the metal toward the vertex C4 and C5 atoms of the heterocycle. Unsuccessful functionalization of the diene moiety by acylation or alkylation of the allylic position indicated the strong stability of these dienes. This stability facilitated the generation of stable and unprecedented conjugated enamine-enol ester- and enamido-enol-Fe(CO)3 complexes, by either kinetic or themodynamic control of the reaction conditions. {\circledC} 2009 American Chemical Society.",
author = "Fernando Ortega-Jim{\'e}nez and Adriana Benavides and Francisco Delgado and Jim{\'e}nez-V{\'a}zquez, {Hugo A.} and Joaqu{\'i}n Tamariz",
year = "2010",
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language = "American English",
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journal = "Organometallics",
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publisher = "American Chemical Society",

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TY - JOUR

T1 - Synthesis and reactivity of η4-diene-Fe(CO)3 complexes from exo-2-oxazolidinone dienes. A facile generation of stable conjugated enol-enamido species

AU - Ortega-Jiménez, Fernando

AU - Benavides, Adriana

AU - Delgado, Francisco

AU - Jiménez-Vázquez, Hugo A.

AU - Tamariz, Joaquín

PY - 2010/1/11

Y1 - 2010/1/11

N2 - A synthesis of new η4 -diene-Fe(CO)3 complexes derived from the novel exo-2-oxazolidinone dienes is described. These complexes were prepared by thermal complexation of the substituted dienes with diiron nonacarbonyl to afford the corresponding complexes as crystal solids. The X-ray single-crystal structure analysis revealed characteristic structural properties for diene-iron complexes, showing that in the conformation of the distorted trigonal-pyramidal geometry two of the carbonyl groups point out from the metal toward the vertex C4 and C5 atoms of the heterocycle. Unsuccessful functionalization of the diene moiety by acylation or alkylation of the allylic position indicated the strong stability of these dienes. This stability facilitated the generation of stable and unprecedented conjugated enamine-enol ester- and enamido-enol-Fe(CO)3 complexes, by either kinetic or themodynamic control of the reaction conditions. © 2009 American Chemical Society.

AB - A synthesis of new η4 -diene-Fe(CO)3 complexes derived from the novel exo-2-oxazolidinone dienes is described. These complexes were prepared by thermal complexation of the substituted dienes with diiron nonacarbonyl to afford the corresponding complexes as crystal solids. The X-ray single-crystal structure analysis revealed characteristic structural properties for diene-iron complexes, showing that in the conformation of the distorted trigonal-pyramidal geometry two of the carbonyl groups point out from the metal toward the vertex C4 and C5 atoms of the heterocycle. Unsuccessful functionalization of the diene moiety by acylation or alkylation of the allylic position indicated the strong stability of these dienes. This stability facilitated the generation of stable and unprecedented conjugated enamine-enol ester- and enamido-enol-Fe(CO)3 complexes, by either kinetic or themodynamic control of the reaction conditions. © 2009 American Chemical Society.

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