Reactivity of chlorinating agents/PPh3 for the chlorination of alcohols and carboxylic acids: a comparative study

Wanchai Pluempanupat; Oraphin Chantarasriwong; Piyada Taboonpong; Doo Ok Jang; Warinthorn Chavasiri

doi:10.1016/j.tetlet.2006.11.060

Reactivity of chlorinating agents/PPh₃ for the chlorination of alcohols and carboxylic acids: a comparative study

Wanchai Pluempanupat, Oraphin Chantarasriwong, Piyada Taboonpong, Doo Ok Jang, Warinthorn Chavasiri

Chemistry and Medical Chemistry

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

11 Citations (Scopus)

Abstract

The reactivity of chlorinating agents was examined with the aid of ¹H NMR using competitive reactions between selected chlorinating agents and CBr₄ towards alcohols and carboxylic acids. The reactivity was greatly dependent on the type of substituent on the chlorinating agents. COCCl₃ and CN substituted trichloromethyl groups enhanced the reactivity of the chlorinating agent with PPh₃ for the chlorination of alcohols and carboxylic acids.

Original language	English
Pages (from-to)	223-226
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	2
DOIs	https://doi.org/10.1016/j.tetlet.2006.11.060
Publication status	Published - 2007 Jan 8

Bibliographical note

Funding Information:
This work was financially supported by a joint research project under the NRCT-KOSEF international cooperative program (KO 47/2547) and the Graduate school, Chulalongkorn University. One of us (D.O.J.) is also grateful for the support from CBMH.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2006.11.060

Cite this

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title = "Reactivity of chlorinating agents/PPh3 for the chlorination of alcohols and carboxylic acids: a comparative study",

abstract = "The reactivity of chlorinating agents was examined with the aid of 1H NMR using competitive reactions between selected chlorinating agents and CBr4 towards alcohols and carboxylic acids. The reactivity was greatly dependent on the type of substituent on the chlorinating agents. COCCl3 and CN substituted trichloromethyl groups enhanced the reactivity of the chlorinating agent with PPh3 for the chlorination of alcohols and carboxylic acids.",

author = "Wanchai Pluempanupat and Oraphin Chantarasriwong and Piyada Taboonpong and Jang, {Doo Ok} and Warinthorn Chavasiri",

note = "Funding Information: This work was financially supported by a joint research project under the NRCT-KOSEF international cooperative program (KO 47/2547) and the Graduate school, Chulalongkorn University. One of us (D.O.J.) is also grateful for the support from CBMH.",

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T1 - Reactivity of chlorinating agents/PPh3 for the chlorination of alcohols and carboxylic acids

T2 - a comparative study

AU - Pluempanupat, Wanchai

AU - Chantarasriwong, Oraphin

AU - Taboonpong, Piyada

AU - Jang, Doo Ok

AU - Chavasiri, Warinthorn

N1 - Funding Information: This work was financially supported by a joint research project under the NRCT-KOSEF international cooperative program (KO 47/2547) and the Graduate school, Chulalongkorn University. One of us (D.O.J.) is also grateful for the support from CBMH.

PY - 2007/1/8

Y1 - 2007/1/8

N2 - The reactivity of chlorinating agents was examined with the aid of 1H NMR using competitive reactions between selected chlorinating agents and CBr4 towards alcohols and carboxylic acids. The reactivity was greatly dependent on the type of substituent on the chlorinating agents. COCCl3 and CN substituted trichloromethyl groups enhanced the reactivity of the chlorinating agent with PPh3 for the chlorination of alcohols and carboxylic acids.

AB - The reactivity of chlorinating agents was examined with the aid of 1H NMR using competitive reactions between selected chlorinating agents and CBr4 towards alcohols and carboxylic acids. The reactivity was greatly dependent on the type of substituent on the chlorinating agents. COCCl3 and CN substituted trichloromethyl groups enhanced the reactivity of the chlorinating agent with PPh3 for the chlorination of alcohols and carboxylic acids.

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