Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

Ali H. Essa; Reinner I. Lerrick; Floriana Tuna; Ross W. Harrington; William Clegg; Michael J. Hall

doi:10.1039/c3cc39147g

Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

Ali H. Essa, Reinner I. Lerrick, Floriana Tuna, Ross W. Harrington, William Clegg, Michael J. Hall

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

Abstract

2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. © The Royal Society of Chemistry 2013.

Original language	English
Pages (from-to)	2756-2758
Number of pages	2
Journal	Chemical Communications
Volume	49
Issue number	27
DOIs	https://doi.org/10.1039/c3cc39147g
Publication status	Published - 7 Apr 2013

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10.1039/c3cc39147g

CCDC 916096: Experimental Crystal Structure Determination
Essa, A. H. (Contributor), Lerrick, R. I. (Contributor), Tuna, F. (Contributor), Harrington, R. W. (Contributor), Clegg, W. (Contributor) & Hall, M. J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/cczr8hg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczr8hg&sid=DataCite
Dataset
CCDC 916100: Experimental Crystal Structure Determination
Essa, A. H. (Contributor), Lerrick, R. I. (Contributor), Tuna, F. (Contributor), Harrington, R. W. (Contributor), Clegg, W. (Contributor) & Hall, M. J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/cczr8ml, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczr8ml&sid=DataCite
Dataset
CCDC 916098: Experimental Crystal Structure Determination
Essa, A. H. (Contributor), Lerrick, R. I. (Contributor), Tuna, F. (Contributor), Harrington, R. W. (Contributor), Clegg, W. (Contributor) & Hall, M. J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2013
DOI: 10.5517/cczr8kj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cczr8kj&sid=DataCite
Dataset

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@article{76af1e4f4095474e897cc726b15297fc,

title = "Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones",

abstract = "2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. {\textcopyright} The Royal Society of Chemistry 2013.",

author = "Essa, {Ali H.} and Lerrick, {Reinner I.} and Floriana Tuna and Harrington, {Ross W.} and William Clegg and Hall, {Michael J.}",

year = "2013",

month = apr,

day = "7",

doi = "10.1039/c3cc39147g",

language = "English",

volume = "49",

pages = "2756--2758",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "27",

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TY - JOUR

T1 - Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

AU - Essa, Ali H.

AU - Lerrick, Reinner I.

AU - Tuna, Floriana

AU - Harrington, Ross W.

AU - Clegg, William

AU - Hall, Michael J.

PY - 2013/4/7

Y1 - 2013/4/7

N2 - 2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. © The Royal Society of Chemistry 2013.

AB - 2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. © The Royal Society of Chemistry 2013.

U2 - 10.1039/c3cc39147g

DO - 10.1039/c3cc39147g

M3 - Article

SN - 1359-7345

VL - 49

SP - 2756

EP - 2758

JO - Chemical Communications

JF - Chemical Communications

IS - 27

ER -

Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

Abstract

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Datasets

CCDC 916096: Experimental Crystal Structure Determination

CCDC 916100: Experimental Crystal Structure Determination

CCDC 916098: Experimental Crystal Structure Determination

Cite this