Mild electrophilic halogenation of chloropyridines using CCl4 or C2Cl6 under basic phase transfer conditions

Ashutosh V. Joshi; Mubeen Baidossi; Nida Qafisheh; Elsa Chachashvili; Yoel Sasson

doi:10.1016/j.tetlet.2004.04.177

Mild electrophilic halogenation of chloropyridines using CCl₄ or C₂Cl₆ under basic phase transfer conditions

Ashutosh V. Joshi, Mubeen Baidossi, Nida Qafisheh, Elsa Chachashvili, Yoel Sasson^*

^*Corresponding author for this work

Institute of Chemistry

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

5 Scopus citations

Abstract

Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50% NaOH or solid K₃PO₄. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.

Original language	English
Pages (from-to)	5061-5063
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.177
State	Published - 21 Jun 2004

Keywords

Aromatic carbanion
Halogenation
Phase transfer
Polyhalomethane
Potassium phosphate

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10.1016/j.tetlet.2004.04.177

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title = "Mild electrophilic halogenation of chloropyridines using CCl4 or C2Cl6 under basic phase transfer conditions",

abstract = "Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50\% NaOH or solid K3PO4. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.",

keywords = "Aromatic carbanion, Halogenation, Phase transfer, Polyhalomethane, Potassium phosphate",

author = "Joshi, \{Ashutosh V.\} and Mubeen Baidossi and Nida Qafisheh and Elsa Chachashvili and Yoel Sasson",

year = "2004",

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doi = "10.1016/j.tetlet.2004.04.177",

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T1 - Mild electrophilic halogenation of chloropyridines using CCl4 or C2Cl6 under basic phase transfer conditions

AU - Joshi, Ashutosh V.

AU - Baidossi, Mubeen

AU - Qafisheh, Nida

AU - Chachashvili, Elsa

AU - Sasson, Yoel

PY - 2004/6/21

Y1 - 2004/6/21

N2 - Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50% NaOH or solid K3PO4. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.

AB - Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50% NaOH or solid K3PO4. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.

KW - Aromatic carbanion

KW - Halogenation

KW - Phase transfer

KW - Polyhalomethane

KW - Potassium phosphate

UR - https://www.scopus.com/pages/publications/2942566154

U2 - 10.1016/j.tetlet.2004.04.177

DO - 10.1016/j.tetlet.2004.04.177

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:2942566154

SN - 0040-4039

VL - 45

SP - 5061

EP - 5063

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Mild electrophilic halogenation of chloropyridines using CCl₄ or C₂Cl₆ under basic phase transfer conditions

Abstract

Keywords

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