The use of BrCCl3-PPh3 in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides

Mariam Al-Azani; Mazen al-Sulaibi; Nuha al Soom; Yosef Al Jasem; Bernhard Bugenhagen; Bassam Al Hindawi; Thies Thiemann

doi:10.1016/j.crci.2016.04.004

The use of BrCCl₃-PPh₃ in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides

Mariam Al-Azani, Mazen al-Sulaibi, Nuha al Soom, Yosef Al Jasem, Bernhard Bugenhagen, Bassam Al Hindawi, Thies Thiemann

Department of Chemistry

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

6 Citations (Scopus)

Abstract

Esters, acyloximes, amides and acid anhydrides have been prepared from the respective carboxylic acids, oximes, amines and alcohols by the use of the reagent combination BrCCl₃-PPh₃. The reactions obviate the handling acyl halides or more aggressive reagents PCl₃, POCl₃, or SOCl₂. Furthermore, the environmentally hazardous CCl₄ used in Appel-type reactions is replaced with BrCCl₃, a reagent of less environmental concern.

Original language	English
Pages (from-to)	921-932
Number of pages	12
Journal	Comptes Rendus Chimie
Volume	19
Issue number	8
DOIs	https://doi.org/10.1016/j.crci.2016.04.004
Publication status	Published - Aug 1 2016

Keywords

Acid anhydrides
Amidation
Appel reaction
Bromotrichlorocarbon
Esterification
O-acyloximes

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

Access to Document

10.1016/j.crci.2016.04.004

Cite this

@article{8f4e20c4470d43a78ceb0dcba7b77092,

title = "The use of BrCCl3-PPh3 in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides",

abstract = "Esters, acyloximes, amides and acid anhydrides have been prepared from the respective carboxylic acids, oximes, amines and alcohols by the use of the reagent combination BrCCl3-PPh3. The reactions obviate the handling acyl halides or more aggressive reagents PCl3, POCl3, or SOCl2. Furthermore, the environmentally hazardous CCl4 used in Appel-type reactions is replaced with BrCCl3, a reagent of less environmental concern.",

keywords = "Acid anhydrides, Amidation, Appel reaction, Bromotrichlorocarbon, Esterification, O-acyloximes",

author = "Mariam Al-Azani and Mazen al-Sulaibi and {al Soom}, Nuha and {Al Jasem}, Yosef and Bernhard Bugenhagen and {Al Hindawi}, Bassam and Thies Thiemann",

note = "Funding Information: Ms. M. Al Azani thanks the UAEU for a PhD scholarship. Publisher Copyright: {\textcopyright} 2016 Acad{\'e}mie des sciences",

year = "2016",

month = aug,

day = "1",

doi = "10.1016/j.crci.2016.04.004",

language = "English",

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journal = "Comptes Rendus Chimie",

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T1 - The use of BrCCl3-PPh3 in Appel type transformations to esters, O-acyloximes, amides, and acid anhydrides

AU - Al-Azani, Mariam

AU - al-Sulaibi, Mazen

AU - al Soom, Nuha

AU - Al Jasem, Yosef

AU - Bugenhagen, Bernhard

AU - Al Hindawi, Bassam

AU - Thiemann, Thies

PY - 2016/8/1

Y1 - 2016/8/1

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AB - Esters, acyloximes, amides and acid anhydrides have been prepared from the respective carboxylic acids, oximes, amines and alcohols by the use of the reagent combination BrCCl3-PPh3. The reactions obviate the handling acyl halides or more aggressive reagents PCl3, POCl3, or SOCl2. Furthermore, the environmentally hazardous CCl4 used in Appel-type reactions is replaced with BrCCl3, a reagent of less environmental concern.

KW - Acid anhydrides

KW - Amidation

KW - Appel reaction

KW - Bromotrichlorocarbon

KW - Esterification

KW - O-acyloximes

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