New synthesis and reactions of a functionalized (η4-butadienyl)tricarbonyliron complexed phosphonate

Patrice Pinsard; Jean Paul Lellouche; Jean Pierre Beaucour; Loïc Toupet; Laurent Schio; René Grée

doi:10.1016/0022-328x(89)88028-3

New synthesis and reactions of a functionalized (η⁴-butadienyl)tricarbonyliron complexed phosphonate

Patrice Pinsard, Jean Paul Lellouche, Jean Pierre Beaucour, Loïc Toupet, Laurent Schio, René Grée

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

20 Scopus citations

Abstract

The reaction of the isolated (η⁵-pentadienyl)tricarbonyliron cation 2 with trimethylphosphite gives not only the (η⁴-butadienyl)tricarbonyliron phosphates 1 and 6 but also the σ-π allyl derivative 7; the unusual regioselectivity of this nucleophilic addition is attributed to the presence of the ester group in 2. A new and efficient synthesis of 1 has been devised based upon the in situ trapping of a transient (η⁵-pentadienyl) complexed cation by P(OMe)₃. The reactions of 1 with two aldehydes have been studied. Low temperature bond-shift isomerizations of the initially-produced trienes complexed by Fe(CO)₃ are observed in several cases.

Original language	English
Pages (from-to)	219-231
Number of pages	13
Journal	Journal of Organometallic Chemistry
Volume	371
Issue number	2
DOIs	https://doi.org/10.1016/0022-328x(89)88028-3
State	Published - 25 Jul 1989
Externally published	Yes

Bibliographical note

Funding Information:
We thank Professor Donaldson for sharing his results with us prior to publication and for fruitful discussions. L-S. thanks Roussel-Uclaf for a fellowship. Partial financial support from CNRS is also gratefully acknowledged.

Funding

We thank Professor Donaldson for sharing his results with us prior to publication and for fruitful discussions. L-S. thanks Roussel-Uclaf for a fellowship. Partial financial support from CNRS is also gratefully acknowledged.

Funders	Funder number
Centre National de la Recherche Scientifique

Access to Document

10.1016/0022-328x(89)88028-3

Cite this

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title = "New synthesis and reactions of a functionalized (η4-butadienyl)tricarbonyliron complexed phosphonate",

abstract = "The reaction of the isolated (η5-pentadienyl)tricarbonyliron cation 2 with trimethylphosphite gives not only the (η4-butadienyl)tricarbonyliron phosphates 1 and 6 but also the σ-π allyl derivative 7; the unusual regioselectivity of this nucleophilic addition is attributed to the presence of the ester group in 2. A new and efficient synthesis of 1 has been devised based upon the in situ trapping of a transient (η5-pentadienyl) complexed cation by P(OMe)3. The reactions of 1 with two aldehydes have been studied. Low temperature bond-shift isomerizations of the initially-produced trienes complexed by Fe(CO)3 are observed in several cases.",

author = "Patrice Pinsard and Lellouche, {Jean Paul} and Beaucour, {Jean Pierre} and Lo{\"i}c Toupet and Laurent Schio and Ren{\'e} Gr{\'e}e",

note = "Funding Information: We thank Professor Donaldson for sharing his results with us prior to publication and for fruitful discussions. L-S. thanks Roussel-Uclaf for a fellowship. Partial financial support from CNRS is also gratefully acknowledged.",

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T1 - New synthesis and reactions of a functionalized (η4-butadienyl)tricarbonyliron complexed phosphonate

AU - Pinsard, Patrice

AU - Lellouche, Jean Paul

AU - Beaucour, Jean Pierre

AU - Toupet, Loïc

AU - Schio, Laurent

AU - Grée, René

N1 - Funding Information: We thank Professor Donaldson for sharing his results with us prior to publication and for fruitful discussions. L-S. thanks Roussel-Uclaf for a fellowship. Partial financial support from CNRS is also gratefully acknowledged.

PY - 1989/7/25

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N2 - The reaction of the isolated (η5-pentadienyl)tricarbonyliron cation 2 with trimethylphosphite gives not only the (η4-butadienyl)tricarbonyliron phosphates 1 and 6 but also the σ-π allyl derivative 7; the unusual regioselectivity of this nucleophilic addition is attributed to the presence of the ester group in 2. A new and efficient synthesis of 1 has been devised based upon the in situ trapping of a transient (η5-pentadienyl) complexed cation by P(OMe)3. The reactions of 1 with two aldehydes have been studied. Low temperature bond-shift isomerizations of the initially-produced trienes complexed by Fe(CO)3 are observed in several cases.

AB - The reaction of the isolated (η5-pentadienyl)tricarbonyliron cation 2 with trimethylphosphite gives not only the (η4-butadienyl)tricarbonyliron phosphates 1 and 6 but also the σ-π allyl derivative 7; the unusual regioselectivity of this nucleophilic addition is attributed to the presence of the ester group in 2. A new and efficient synthesis of 1 has been devised based upon the in situ trapping of a transient (η5-pentadienyl) complexed cation by P(OMe)3. The reactions of 1 with two aldehydes have been studied. Low temperature bond-shift isomerizations of the initially-produced trienes complexed by Fe(CO)3 are observed in several cases.

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