Radical reactions using decacarbonyldimanganese under biphasic conditions

N  Huther; P T  McGrail; A F  Parsons

doi:10.1002/ejoc.200400025

Radical reactions using decacarbonyldimanganese under biphasic conditions

N Huther, P T McGrail, A F Parsons

Chemistry

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

Abstract

Radical reactions of alkyl halides, initiated by photolysis in the presence of decacarbonyldimanganese, can be performed in biphasic media. Reactions in the presence of aqueous sodium hydroxide together with a phase-transfer catalyst result in the efficient removal of manganese halide by-products and also lead to the regeneration of decacarbonyldimanganese. A range of efficient radical couplings, cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition-ionic cyclisation sequence that was employed in a short approach to (+/-)-coronamic acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

Original language	English
Pages (from-to)	1740-1749
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2004
Issue number	8
DOIs	https://doi.org/10.1002/ejoc.200400025
Publication status	Published - Apr 2004

Keywords

cyclization
manganese
heterocycles
phase-transfer catalysis
radical reactions
PHASE-TRANSFER CONDITIONS
DIMANGANESE DECACARBONYL
CONVENIENT SYNTHESIS
AQUEOUS-MEDIA
MANGANESE
CARBONYL
ACID
PHOTOCHEMISTRY
DERIVATIVES
HALIDES

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10.1002/ejoc.200400025

http://dx.doi.org/10.1002/ejoc.200400025

Cite this

@article{da9332886eea43f3b3617ec91e4c0a5c,

title = "Radical reactions using decacarbonyldimanganese under biphasic conditions",

abstract = "Radical reactions of alkyl halides, initiated by photolysis in the presence of decacarbonyldimanganese, can be performed in biphasic media. Reactions in the presence of aqueous sodium hydroxide together with a phase-transfer catalyst result in the efficient removal of manganese halide by-products and also lead to the regeneration of decacarbonyldimanganese. A range of efficient radical couplings, cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition-ionic cyclisation sequence that was employed in a short approach to (+/-)-coronamic acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).",

keywords = "cyclization, manganese, heterocycles, phase-transfer catalysis, radical reactions, PHASE-TRANSFER CONDITIONS, DIMANGANESE DECACARBONYL, CONVENIENT SYNTHESIS, AQUEOUS-MEDIA, MANGANESE, CARBONYL, ACID, PHOTOCHEMISTRY, DERIVATIVES, HALIDES",

author = "N Huther and McGrail, {P T} and Parsons, {A F}",

year = "2004",

month = apr,

doi = "10.1002/ejoc.200400025",

language = "English",

volume = "2004",

pages = "1740--1749",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-Blackwell",

number = "8",

}

TY - JOUR

T1 - Radical reactions using decacarbonyldimanganese under biphasic conditions

AU - Huther, N

AU - McGrail, P T

AU - Parsons, A F

PY - 2004/4

Y1 - 2004/4

N2 - Radical reactions of alkyl halides, initiated by photolysis in the presence of decacarbonyldimanganese, can be performed in biphasic media. Reactions in the presence of aqueous sodium hydroxide together with a phase-transfer catalyst result in the efficient removal of manganese halide by-products and also lead to the regeneration of decacarbonyldimanganese. A range of efficient radical couplings, cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition-ionic cyclisation sequence that was employed in a short approach to (+/-)-coronamic acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

AB - Radical reactions of alkyl halides, initiated by photolysis in the presence of decacarbonyldimanganese, can be performed in biphasic media. Reactions in the presence of aqueous sodium hydroxide together with a phase-transfer catalyst result in the efficient removal of manganese halide by-products and also lead to the regeneration of decacarbonyldimanganese. A range of efficient radical couplings, cyclisations and intermolecular addition reactions were performed under these conditions. This included the development of a new tandem radical addition-ionic cyclisation sequence that was employed in a short approach to (+/-)-coronamic acid. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

KW - cyclization

KW - manganese

KW - heterocycles

KW - phase-transfer catalysis

KW - radical reactions

KW - PHASE-TRANSFER CONDITIONS

KW - DIMANGANESE DECACARBONYL

KW - CONVENIENT SYNTHESIS

KW - AQUEOUS-MEDIA

KW - MANGANESE

KW - CARBONYL

KW - ACID

KW - PHOTOCHEMISTRY

KW - DERIVATIVES

KW - HALIDES

U2 - 10.1002/ejoc.200400025

DO - 10.1002/ejoc.200400025

M3 - Article

VL - 2004

SP - 1740

EP - 1749

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 8

ER -