Influence of palladium(II) complexes on the cycloaddition of α-bromoalkyl ketenes to cyclopentadiene

Ian J.S. Fairlamb; Julia M. Dickinson; Ileana M. Cristea

doi:10.1016/S0040-4020(01)00092-8

Influence of palladium(II) complexes on the cycloaddition of α-bromoalkyl ketenes to cyclopentadiene

Ian J.S. Fairlamb, Julia M. Dickinson, Ileana M. Cristea

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

7 Scopus citations

Abstract

Palladium(II) complexes, of the type PdL₂X₂ and PdX₂, influence both the yields and endo/exo ratio in formation of several 7-bromo-7-alkylbicyclo[3.2.0]hept-2-en-6-ones. Standard dehydrochlorination of α-bromoacyl chlorides with triethylamine in the presence of cyclopentadiene and palladium catalyst promotes the formation of the exo cycloadducts, which is accompanied by an improvement in the yields for both endo and exo cycloadducts. The mechanism of the palladium-mediated cycloaddition is discussed.

Original language	English (US)
Pages (from-to)	2237-2246
Number of pages	10
Journal	Tetrahedron
Volume	57
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(01)00092-8
State	Published - Mar 10 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Acyl chlorides
Bicyclic compounds
Cycloadditions
Cyclopentadiene
Palladium

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10.1016/S0040-4020(01)00092-8

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title = "Influence of palladium(II) complexes on the cycloaddition of α-bromoalkyl ketenes to cyclopentadiene",

abstract = "Palladium(II) complexes, of the type PdL2X2 and PdX2, influence both the yields and endo/exo ratio in formation of several 7-bromo-7-alkylbicyclo[3.2.0]hept-2-en-6-ones. Standard dehydrochlorination of α-bromoacyl chlorides with triethylamine in the presence of cyclopentadiene and palladium catalyst promotes the formation of the exo cycloadducts, which is accompanied by an improvement in the yields for both endo and exo cycloadducts. The mechanism of the palladium-mediated cycloaddition is discussed.",

keywords = "Acyl chlorides, Bicyclic compounds, Cycloadditions, Cyclopentadiene, Palladium",

author = "Fairlamb, {Ian J.S.} and Dickinson, {Julia M.} and Cristea, {Ileana M.}",

note = "Funding Information: We wish to thank the Manchester Metropolitan University for a PhD studentship for I. J. S. F and TEMPUS for a grant to I. M. C. We would like to thank Mr Paul Foulds and Dr David G. Kelly for informative discussions. We gratefully acknowledge Dr Thomas Tidewell for interesting thoughts on the reactivity of alkylketenes and Dr Guy C. Lloyd-Jones for valuable discussion of possible palladium mechanisms. ",

year = "2001",

month = mar,

day = "10",

doi = "10.1016/S0040-4020(01)00092-8",

language = "English (US)",

volume = "57",

pages = "2237--2246",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "11",

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TY - JOUR

T1 - Influence of palladium(II) complexes on the cycloaddition of α-bromoalkyl ketenes to cyclopentadiene

AU - Fairlamb, Ian J.S.

AU - Dickinson, Julia M.

AU - Cristea, Ileana M.

N1 - Funding Information: We wish to thank the Manchester Metropolitan University for a PhD studentship for I. J. S. F and TEMPUS for a grant to I. M. C. We would like to thank Mr Paul Foulds and Dr David G. Kelly for informative discussions. We gratefully acknowledge Dr Thomas Tidewell for interesting thoughts on the reactivity of alkylketenes and Dr Guy C. Lloyd-Jones for valuable discussion of possible palladium mechanisms.

PY - 2001/3/10

Y1 - 2001/3/10

N2 - Palladium(II) complexes, of the type PdL2X2 and PdX2, influence both the yields and endo/exo ratio in formation of several 7-bromo-7-alkylbicyclo[3.2.0]hept-2-en-6-ones. Standard dehydrochlorination of α-bromoacyl chlorides with triethylamine in the presence of cyclopentadiene and palladium catalyst promotes the formation of the exo cycloadducts, which is accompanied by an improvement in the yields for both endo and exo cycloadducts. The mechanism of the palladium-mediated cycloaddition is discussed.

AB - Palladium(II) complexes, of the type PdL2X2 and PdX2, influence both the yields and endo/exo ratio in formation of several 7-bromo-7-alkylbicyclo[3.2.0]hept-2-en-6-ones. Standard dehydrochlorination of α-bromoacyl chlorides with triethylamine in the presence of cyclopentadiene and palladium catalyst promotes the formation of the exo cycloadducts, which is accompanied by an improvement in the yields for both endo and exo cycloadducts. The mechanism of the palladium-mediated cycloaddition is discussed.

KW - Acyl chlorides

KW - Bicyclic compounds

KW - Cycloadditions

KW - Cyclopentadiene

KW - Palladium

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U2 - 10.1016/S0040-4020(01)00092-8

DO - 10.1016/S0040-4020(01)00092-8

M3 - Article

AN - SCOPUS:0035835943

SN - 0040-4020

VL - 57

SP - 2237

EP - 2246

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Influence of palladium(II) complexes on the cycloaddition of α-bromoalkyl ketenes to cyclopentadiene

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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