Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system

D J  Adams; J H  Clark; H  McFarland; D J  Nightingale

Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system

D J Adams, J H Clark, H McFarland, D J Nightingale

Chemistry

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

Abstract

Reactions of chloro- and nitro-aromatics with low water content solutions of TMAF in DMSO can lead to complex product mixtures resulting from activation of DMSO by fluoride and the formation of DMSO-derived products. Also, the system has been shown to give hydrolysis products in addition to the well-known ethers and phenols, with carboxylic acids and benzamides being formed from the attempted fluorodenitration of substituted benzonitriles. (C) 1999 Elsevier Science S.A. All rights reserved.

Original language	English
Pages (from-to)	51-55
Number of pages	5
Journal	JOURNAL OF FLUORINE CHEMISTRY
Volume	94
Issue number	1
Publication status	Published - 11 Feb 1999

Keywords

tetramethylammonium fluoride
dimethylsulphoxide
base catalysis
diphenylmethane
benzonitrile
ORGANIC-SYNTHESIS
ARYL FLUORIDES
CHLORIDE
ION

Cite this

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title = "Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system",

abstract = "Reactions of chloro- and nitro-aromatics with low water content solutions of TMAF in DMSO can lead to complex product mixtures resulting from activation of DMSO by fluoride and the formation of DMSO-derived products. Also, the system has been shown to give hydrolysis products in addition to the well-known ethers and phenols, with carboxylic acids and benzamides being formed from the attempted fluorodenitration of substituted benzonitriles. (C) 1999 Elsevier Science S.A. All rights reserved.",

keywords = "tetramethylammonium fluoride, dimethylsulphoxide, base catalysis, diphenylmethane, benzonitrile, ORGANIC-SYNTHESIS, ARYL FLUORIDES, CHLORIDE, ION",

author = "Adams, {D J} and Clark, {J H} and H McFarland and Nightingale, {D J}",

year = "1999",

month = feb,

day = "11",

language = "English",

volume = "94",

pages = "51--55",

journal = "JOURNAL OF FLUORINE CHEMISTRY",

issn = "0022-1139",

publisher = "Elsevier B.V.",

number = "1",

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TY - JOUR

T1 - Unexpected side products in the tetramethylammonium fluoride-dimethylsulphoxide system

AU - Adams, D J

AU - Clark, J H

AU - McFarland, H

AU - Nightingale, D J

PY - 1999/2/11

Y1 - 1999/2/11

N2 - Reactions of chloro- and nitro-aromatics with low water content solutions of TMAF in DMSO can lead to complex product mixtures resulting from activation of DMSO by fluoride and the formation of DMSO-derived products. Also, the system has been shown to give hydrolysis products in addition to the well-known ethers and phenols, with carboxylic acids and benzamides being formed from the attempted fluorodenitration of substituted benzonitriles. (C) 1999 Elsevier Science S.A. All rights reserved.

AB - Reactions of chloro- and nitro-aromatics with low water content solutions of TMAF in DMSO can lead to complex product mixtures resulting from activation of DMSO by fluoride and the formation of DMSO-derived products. Also, the system has been shown to give hydrolysis products in addition to the well-known ethers and phenols, with carboxylic acids and benzamides being formed from the attempted fluorodenitration of substituted benzonitriles. (C) 1999 Elsevier Science S.A. All rights reserved.

KW - tetramethylammonium fluoride

KW - dimethylsulphoxide

KW - base catalysis

KW - diphenylmethane

KW - benzonitrile

KW - ORGANIC-SYNTHESIS

KW - ARYL FLUORIDES

KW - CHLORIDE

KW - ION

M3 - Article

SN - 0022-1139

VL - 94

SP - 51

EP - 55

JO - JOURNAL OF FLUORINE CHEMISTRY

JF - JOURNAL OF FLUORINE CHEMISTRY

IS - 1

ER -