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

Journal of the American Chemical Society

Aromatic cation activation of alcohols: conversion to alkyl chlorides using dichlorodiphenylcyclopropene

BD Kelly, TH Lambert

Index: Kelly, Brendan D.; Lambert, Tristan H. Journal of the American Chemical Society, 2009 , vol. 131, # 39 p. 13930 - 13931

Full Text: HTML

Citation Number: 42

Abstract

A novel paradigm for the activation of alcohols toward nucleophilic displacement via formation of cyclopropenium ethers is described. The conversion of a range of alcohol substrates to the corresponding alkyl chlorides occurs rapidly upon treatment with 3, 3- dichloro-1, 2-diphenylcyclopropene. 1H NMR data support the intermediacy of a cyclopropenium intermediate, and the reaction is demonstrated to proceed primarily via ...

2-Octyn-1-ol Structure

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~90%

1-Chloro-2-octyne Structure

1-Chloro-2-octyne

DPC Structure

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3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

2-cyclohexenol Structure

~90%

1-Chloro-2-octyne Structure

1-Chloro-2-octyne

DPC Structure

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1-Phenyl-2-propanol Structure

1-Phenyl-2-propanol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~92%

Benzene,(2-chloropropyl) Structure

Benzene,(2-chlo...

DPC Structure

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Cinnamyl alcohol Structure

Cinnamyl alcohol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

DPC Structure

(3-Chloro-1-propen-1-yl)benzene Structure

(3-Chloro-1-pro...

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3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

Benzyl alcohol Structure

~0%

Benzyl chloride Structure

Benzyl chloride

DPC Structure

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2-Octyn-1-ol Structure

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

1-Chloro-2-octyne Structure

1-Chloro-2-octyne

DPC Structure

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1-Phenyl-2-propanol Structure

1-Phenyl-2-propanol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

Benzene,(2-chloropropyl) Structure

Benzene,(2-chlo...

DPC Structure

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Methylbenzylalcohol Structure

Methylbenzylalcohol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

GY1&R Structure

DPC Structure

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(±)-1-phenylethanol Structure

(±)-1-phenylethanol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

(R)-1-chloro-1-phenylethane Structure

(R)-1-chloro-1-...

DPC Structure

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3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

Methyl (2S)-hydroxy(phenyl)acetate Structure

Methyl (2S)-hyd...

~0%

Benzeneacetic acid, a-chloro-, methyl ester Structure

Benzeneacetic a...

DPC Structure

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3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

citrol Structure

~0%

1-chloro-3,7-dimethylocta-2,6-diene Structure

1-chloro-3,7-di...

DPC Structure

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acetic acid 4-hydroxybut-2-enyl ester Structure

acetic acid 4-h...

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

(Z)-4-chlorobut-2-en-1-yl acetate Structure

(Z)-4-chlorobut...

DPC Structure

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2-Octanol Structure

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

DPC Structure

Octane, 2-chloro Structure

Octane, 2-chloro

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Phenethyl alcohol Structure

Phenethyl alcohol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~0%

(2-Chloroethyl)benzene Structure

(2-Chloroethyl)...

DPC Structure

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3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

2-cyclohexenol Structure

~0%

1-Chloro-2-octyne Structure

1-Chloro-2-octyne

DPC Structure

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2-Methyl-1-phenyl-2-propanol Structure

2-Methyl-1-phen...

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~45%

Benzene,(2-methyl-1-propen-1-yl) Structure

Benzene,(2-meth...

(2-chloro-2-methyl-propyl)benzene Structure

(2-chloro-2-met...

Detail Learn More

Phenethyl alcohol Structure

Phenethyl alcohol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~89%

(2-Chloroethyl)benzene Structure

(2-Chloroethyl)...

DPC Structure

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Methylbenzylalcohol Structure

Methylbenzylalcohol

3,3-dichloro-1,2-diphenylcyclopropene Structure

3,3-dichloro-1,...

~91%

GY1&R Structure

DPC Structure

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The Dielectric Properties of Acetylenic Compounds. V. Acetyl...

[Toussaint; Wenzke Journal of the American Chemical Society, 1935 , vol. 57, p. 668]

768. Studies with acetylenes. Part II. Some reactions of Gri...

[Nigam; Weedon Journal of the Chemical Society, 1957 , p. 3868,3872]