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On the nucleophilic tele-substitution of dichloropyrazines by metallated dithianes

On the nucleophilic tele-substitution of dichloropyrazines by metallated dithianes
On the nucleophilic tele-substitution of dichloropyrazines by metallated dithianes
The reaction of dichloropyrazines with a dithiane anion gave isomers of the expected formylated chloropyrazines after deprotection with methyl iodide. A tele-substitution mechanism accounts for these observations and is supported by deuterium labelling studies.
pyrazines, dithianes, tele-substitution, metallation directed metalation, diazines pyridines, benzodiazines, pyridazines, pyrimidines, carbolines, quinolines, azines
0040-4039
31-34
Torr, Jane E.
47909823-e298-47d1-90ff-8ebb949d57cd
Large, Jonathan M.
d9c1378f-6ee3-4e1b-abf7-0fffa6a5fbf2
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
McDonald, Edward
99fa0e30-4f4f-4814-8450-75e087ba3018
Torr, Jane E.
47909823-e298-47d1-90ff-8ebb949d57cd
Large, Jonathan M.
d9c1378f-6ee3-4e1b-abf7-0fffa6a5fbf2
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
McDonald, Edward
99fa0e30-4f4f-4814-8450-75e087ba3018

Torr, Jane E., Large, Jonathan M., Horton, Peter N., Hursthouse, Michael B. and McDonald, Edward (2006) On the nucleophilic tele-substitution of dichloropyrazines by metallated dithianes. Tetrahedron Letters, 47 (1), 31-34. (doi:10.1016/j.tetlet.2005.10.146).

Record type: Article

Abstract

The reaction of dichloropyrazines with a dithiane anion gave isomers of the expected formylated chloropyrazines after deprotection with methyl iodide. A tele-substitution mechanism accounts for these observations and is supported by deuterium labelling studies.

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More information

Published date: 2006
Keywords: pyrazines, dithianes, tele-substitution, metallation directed metalation, diazines pyridines, benzodiazines, pyridazines, pyrimidines, carbolines, quinolines, azines

Identifiers

Local EPrints ID: 44557
URI: http://eprints.soton.ac.uk/id/eprint/44557
ISSN: 0040-4039
PURE UUID: 909e9567-7018-4fcd-b62f-52a0a9a6d3ef
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

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Date deposited: 28 Feb 2007
Last modified: 05 Nov 2019 01:55

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Contributors

Author: Jane E. Torr
Author: Jonathan M. Large
Author: Peter N. Horton ORCID iD
Author: Edward McDonald

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