Bromination and alkylation of tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes

Ming Chang P. Yeh; Chong Chen Hwu

doi:10.1016/0022-328X(91)80247-H

Bromination and alkylation of tricarbonyl(η¹,η²-but-3-en-1-yl)iron(O) anion complexes

Ming Chang P. Yeh^*
, Chong Chen Hwu

^*Corresponding author for this work

Department of Chemistry

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

18 Citations (Scopus)

Abstract

Reactive carbon nucleophiles add to tricarbonyl(η⁴-1,3-diene)iron(O) complexes at -78°C to produce putative internally coordinated tricarbonyl(η¹,η²-but-3-en-1-yl)iron(O) anion complexes. Treatment of the reactive intermediates with bromine, followed by an aqueous process, leads to γ,δ-unsaturated acids. Reaction of the intermediates with iodomethane or benzyl bromide gives γ,δ-unsaturated ketones after carbonyl insertions. Benzoyl chloride is also observed to react with the postulate intermediates to form γ,δ-unsaturated benzophenone derivatives.

Original language	English
Pages (from-to)	341-355
Number of pages	15
Journal	Journal of Organometallic Chemistry
Volume	419
Issue number	3
DOIs	https://doi.org/10.1016/0022-328X(91)80247-H
Publication status	Published - 1991

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/0022-328X(91)80247-H

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@article{88bf6d564d484c8c96be528825ede809,

title = "Bromination and alkylation of tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes",

abstract = "Reactive carbon nucleophiles add to tricarbonyl(η4-1,3-diene)iron(O) complexes at -78°C to produce putative internally coordinated tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes. Treatment of the reactive intermediates with bromine, followed by an aqueous process, leads to γ,δ-unsaturated acids. Reaction of the intermediates with iodomethane or benzyl bromide gives γ,δ-unsaturated ketones after carbonyl insertions. Benzoyl chloride is also observed to react with the postulate intermediates to form γ,δ-unsaturated benzophenone derivatives.",

author = "Yeh, \{Ming Chang P.\} and Hwu, \{Chong Chen\}",

note = "Funding Information: Financial support for this research was provided by the National Science Council R.O.C. (NSC 80-0.208-M003-18W).e are grateful to the Departmento f Chemistry,A cademiaS inica for assistancew ith the 200 MHz NMR spectrometer and high resolutionm asss pectrald eterminations.",

year = "1991",

doi = "10.1016/0022-328X(91)80247-H",

language = "English",

volume = "419",

pages = "341--355",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier BV",

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T1 - Bromination and alkylation of tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes

AU - Yeh, Ming Chang P.

AU - Hwu, Chong Chen

N1 - Funding Information: Financial support for this research was provided by the National Science Council R.O.C. (NSC 80-0.208-M003-18W).e are grateful to the Departmento f Chemistry,A cademiaS inica for assistancew ith the 200 MHz NMR spectrometer and high resolutionm asss pectrald eterminations.

PY - 1991

Y1 - 1991

N2 - Reactive carbon nucleophiles add to tricarbonyl(η4-1,3-diene)iron(O) complexes at -78°C to produce putative internally coordinated tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes. Treatment of the reactive intermediates with bromine, followed by an aqueous process, leads to γ,δ-unsaturated acids. Reaction of the intermediates with iodomethane or benzyl bromide gives γ,δ-unsaturated ketones after carbonyl insertions. Benzoyl chloride is also observed to react with the postulate intermediates to form γ,δ-unsaturated benzophenone derivatives.

AB - Reactive carbon nucleophiles add to tricarbonyl(η4-1,3-diene)iron(O) complexes at -78°C to produce putative internally coordinated tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes. Treatment of the reactive intermediates with bromine, followed by an aqueous process, leads to γ,δ-unsaturated acids. Reaction of the intermediates with iodomethane or benzyl bromide gives γ,δ-unsaturated ketones after carbonyl insertions. Benzoyl chloride is also observed to react with the postulate intermediates to form γ,δ-unsaturated benzophenone derivatives.

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UR - https://www.scopus.com/pages/publications/0000196239#tab=citedBy

U2 - 10.1016/0022-328X(91)80247-H

DO - 10.1016/0022-328X(91)80247-H

M3 - Article

AN - SCOPUS:0000196239

SN - 0022-328X

VL - 419

SP - 341

EP - 355

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 3

ER -

Bromination and alkylation of tricarbonyl(η¹,η²-but-3-en-1-yl)iron(O) anion complexes

Abstract

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