Bromination and alkylation of tricarbonyl(η12-but-3-en-1-yl)iron(O) anion complexes

Ming-Chang P. Yeh, Chong Chen Hwu

Research output: Contribution to journalArticle

17 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(η12-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 languageEnglish
Pages (from-to)341-355
Number of pages15
JournalJournal of Organometallic Chemistry
Volume419
Issue number3
DOIs
Publication statusPublished - 1991 Jan 1

Fingerprint

bromination
Halogenation
alkylation
Alkylation
Anions
Negative ions
Iron
anions
iron
Bromine
Nucleophiles
nucleophiles
dienes
bromine
axioms
Ketones
ketones
bromides
insertion
Carbon

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Bromination and alkylation of tricarbonyl(η12-but-3-en-1-yl)iron(O) anion complexes. / Yeh, Ming-Chang P.; Hwu, Chong Chen.

In: Journal of Organometallic Chemistry, Vol. 419, No. 3, 01.01.1991, p. 341-355.

Research output: Contribution to journalArticle

@article{b60cff2f2a264a9f9964823de05ad4a3,
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}",
year = "1991",
month = "1",
day = "1",
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",
number = "3",

}

TY - JOUR

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

PY - 1991/1/1

Y1 - 1991/1/1

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.

UR - http://www.scopus.com/inward/record.url?scp=0000196239&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000196239&partnerID=8YFLogxK

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

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

M3 - Article

AN - SCOPUS:0000196239

VL - 419

SP - 341

EP - 355

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 3

ER -