e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A Product Analytical Study of the Thermal and Photolytic Decomposition of Some Arenediazonium Salts in Solution.

PSJ Canning, H Maskill, K McCrudden…

Index: Canning, Peter S. J.; Maskill, Howard; McCrudden, Katharine; Sexton, Brian Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 4 p. 789 - 800

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Citation Number: 33

Abstract

Products of thermal and photochemical reactions of eleven arenediazonium tetrafluoroborates in various solvents have been analyzed. All compounds in most solvents undergo unimolecular heterolysis to give singlet aryl cations which are captured by solvent. This mechanism is dominant for arenediazonium ions without electron-withdrawing substituents in all solvents, and the only reaction observed in water. Additionally, ...

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

Benzenediazonium chloride Structure

Benzenediazoniu...

~%

Fluorobenzene Structure

2-Phenoxy-1,1,1-trifluoroethane Structure

2-Phenoxy-1,1,1...

2-fluorobenzenediazonium tetrafluoroborate Structure

2-fluorobenzene...

~%

Fluorobenzene Structure

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

Benzenediazonium tetrafluoroborate Structure

Benzenediazoniu...

~%

Fluorobenzene Structure

2-Phenoxy-1,1,1-trifluoroethane Structure

2-Phenoxy-1,1,1...

Benzenediazonium tetrafluoroborate Structure

Benzenediazoniu...

trifluoroacetic acid Structure

trifluoroacetic acid

~4%

Fluorobenzene Structure

PHENYL TRIFLUOROACETATE Structure

PHENYL TRIFLUOR...

Ethanol Structure

Benzenediazonium tetrafluoroborate Structure

Benzenediazoniu...

~2%

Fluorobenzene Structure

phenetole Structure

Detail

2-Fluoroethanol Structure

2-Fluoroethanol

m-methylbenzenediazonium tetrafluoroborate Structure

m-methylbenzene...

~1%

Fluorobenzene Structure

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Detail

Ethanol Structure

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~%

Fluorobenzene Structure

PHENETOLE, M-FLUORO- Structure

PHENETOLE, M-FLUORO-

2-Fluoroethanol Structure

2-Fluoroethanol

Benzenediazonium tetrafluoroborate Structure

Benzenediazoniu...

~36%

Fluorobenzene Structure

(2-FLUOROETHOXY)-BENZENE Structure

(2-FLUOROETHOXY...

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~7%

3-Fluorophenol Structure

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Detail

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~%

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

1-fluoro-3-(2,2,2-trifluoroethoxy)benzene Structure

1-fluoro-3-(2,2...

2-Fluoroethanol Structure

2-Fluoroethanol

m-methylbenzenediazonium tetrafluoroborate Structure

m-methylbenzene...

~31%

Fluorobenzene Structure

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Detail

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~31%

3-Fluorophenol Structure

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Detail

4-Methoxybenzenediazonium tetrafluoroborate Structure

4-Methoxybenzen...

~96%

Mequinol Structure

2-Fluoroethanol Structure

2-Fluoroethanol

Benzenediazonium tetrafluoroborate Structure

Benzenediazoniu...

~63%

Fluorobenzene Structure

(2-FLUOROETHOXY)-BENZENE Structure

(2-FLUOROETHOXY...

Benzenediazonium, 4-fluoro-, tetrafluoroborate(1-) Structure

Benzenediazoniu...

~99%

4-Fluorophenol Structure

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~59%

3-Fluorophenol Structure

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Detail

tetrafluoroborate of 3-trifluoromethylbenzenediazonium Structure

tetrafluorobora...

trifluoroacetic acid Structure

trifluoroacetic acid

~18%

3-Fluorobenzotrifluoride Structure

3-Fluorobenzotr...

(3-Trifluoromethyl-phenyl)trifluoroacetate Structure

(3-Trifluoromet...

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

4-Methoxybenzenediazonium tetrafluoroborate Structure

4-Methoxybenzen...

~64%

4-Fluorobenzyl alcohol Structure

4-Fluorobenzyl ...

1-methoxy-4-(2,2,2-trifluoroethoxy)benzene Structure

1-methoxy-4-(2,...

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

4-Methoxybenzenediazonium tetrafluoroborate Structure

4-Methoxybenzen...

~35%

4-Fluorobenzyl alcohol Structure

4-Fluorobenzyl ...

1-methoxy-4-(2,2,2-trifluoroethoxy)benzene Structure

1-methoxy-4-(2,...

3-Fluorophenol Structure

Ethyl 4-methylbenzenesulfonate Structure

Ethyl 4-methylb...

~%

PHENETOLE, M-FLUORO- Structure

PHENETOLE, M-FLUORO-

Ethanol Structure

3-fluorobenzenediazonium tetrafluoroborate Structure

3-fluorobenzene...

~%

Fluorobenzene Structure

PHENETOLE, M-FLUORO- Structure

PHENETOLE, M-FLUORO-

Ethanol Structure

m-methylbenzenediazonium tetrafluoroborate Structure

m-methylbenzene...

~80%

3-Fluorotoluene Structure

3-Fluorotoluene

Benzene, 1-ethoxy-3-methyl- Structure

Benzene, 1-etho...

Detail

2,2,2-Trifluoroethanol Structure

2,2,2-Trifluoro...

3-nitrobenzene-1-diazonium tertafluoroborate Structure

3-nitrobenzene-...

~%

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

1-Nitro-3-(2,2,2-trifluoroethoxy)benzene Structure

1-Nitro-3-(2,2,...

3-nitrobenzene-1-diazonium tertafluoroborate Structure

3-nitrobenzene-...

trifluoroacetic acid Structure

trifluoroacetic acid

~8%

3-Fluoronitrobenzene Structure

3-Fluoronitrobenzene

Acetic acid, 2,2,2-trifluoro-, 3-nitrophenyl ester Structure

Acetic acid, 2,...

Mechanistic Studies on Fluorobenzene Synthesis from 1, 1-Dif...

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A series of NiM (M= Ru, Rh, and Pd) bimetallic catalysts for...

[Chatterjee, Maya; Ishizaka, Takayuki; Suzuki, Akira; Kawanami, Hajime Chemical Communications, 2013 , vol. 49, # 40 p. 4567 - 4569]

Electroreductive dehalogenation of fluorobenzenes

[Kariv-Miller, Essie; Vajtner, Zlatko Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1394 - 1399]

Aryl fluorides from the reaction of boron trifluoride with a...

[Meio, Giuseppe V. De; Pinhey, John T. Journal of the Chemical Society, Chemical Communications, 1990 , # 15 p. 1065 - 1066]

Mechanistic Studies on Fluorobenzene Synthesis from 1, 1-Dif...

[Tojo, Masahiro; Fukuoka, Shinsuke; Tsukube, Hiroshi Bulletin of the Chemical Society of Japan, 2011 , vol. 84, # 3 p. 333 - 340]