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The Journal of Organic Chemistry

Carbon-hydrogen vs. carbon-carbon bond cleavage of 1, 2-diarylethane radical cations in acetonitrile-water

DM Camaioni, JA Franz

Index: Camaioni, Donald M.; Franz, James A. Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1607 - 1613

Full Text: HTML

Citation Number: 50

Abstract

R-+ Cu (I1)-+ RCu (II1)-ROH+ CU (I)+ H+(8) of the radical cations, are oxidized to hydroxylic products by Cu2+ ions,* J5 and Cu+ ions, so formed, propagate the oxidation by regenerating SO4-., eq 7. As depicted in Scheme I, alkyl-substituted radical cations undergo competing reactions of side chain fragmentation and hydration. Though hydration is rapid, side chain fragmentation is favored in acidic media because dehydration of the hydroxyl ...

Bibenzyl Structure

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

4-Phenethylphenol Structure

4-Phenethylphenol

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

Phenol,4-(2-phenylethenyl)- Structure

Phenol,4-(2-phe...

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

Benzaldehyde Structure

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

Detail

Bibenzyl Structure

~%

2-(2-phenylethyl)phenol Structure

2-(2-phenylethy...

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Detail

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

~%

p-tolylmethanol Structure

p-tolylmethanol

1,2-di-p-tolylethan-1-ol Structure

1,2-di-p-tolyle...

p-Tolualdehyde Structure

Detail

4-Methylbenzyl bromide Structure

4-Methylbenzyl ...

~%

N-[1,2-bis(4-methylphenyl)ethyl]acetamide Structure

N-[1,2-bis(4-me...

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

~%

p-tolylmethanol Structure

p-tolylmethanol

1,2-di-p-tolylethan-1-ol Structure

1,2-di-p-tolyle...

p-Tolualdehyde Structure

Detail

Bibenzyl Structure

~%

2-(2-phenylethyl)phenol Structure

2-(2-phenylethy...

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Detail

Bibenzyl Structure

~%

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Benzaldehyde Structure

Detail

Bibenzyl Structure

~%

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Detail

Bibenzyl Structure

~%

2-(2-phenylethyl)phenol Structure

2-(2-phenylethy...

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Detail

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

~%

p-tolylmethanol Structure

p-tolylmethanol

1,2-di-p-tolylethan-1-ol Structure

1,2-di-p-tolyle...

p-Tolualdehyde Structure

Detail

4-Methylbenzyl bromide Structure

4-Methylbenzyl ...

~%

[4-[2-(4-methylphenyl)ethyl]phenyl]methanol Structure

[4-[2-(4-methyl...

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

~%

p-tolylmethanol Structure

p-tolylmethanol

1,2-di-p-tolylethan-1-ol Structure

1,2-di-p-tolyle...

p-Tolualdehyde Structure

Detail

4-[2-(4-methylphenyl)ethyl]benzoic acid Structure

4-[2-(4-methylp...

~%

[4-[2-(4-methylphenyl)ethyl]phenyl]methanol Structure

[4-[2-(4-methyl...

1-chloro-4-[2-(4-methylphenyl)ethyl]benzene Structure

1-chloro-4-[2-(...

~%

[4-[2-(4-methylphenyl)ethyl]phenyl]methanol Structure

[4-[2-(4-methyl...

(4-Methylbenzyl)(triphenyl)phosphonium bromide Structure

(4-Methylbenzyl...

~%

[4-[2-(4-methylphenyl)ethyl]phenyl]methanol Structure

[4-[2-(4-methyl...

(Z)-1-(4-chlorophenyl)-2-(4-methylphenyl)ethene Structure

(Z)-1-(4-chloro...

~%

[4-[2-(4-methylphenyl)ethyl]phenyl]methanol Structure

[4-[2-(4-methyl...

(Z)-1-(4-chlorophenyl)-2-(4-methylphenyl)ethene Structure

(Z)-1-(4-chloro...

~%

1-chloro-4-[2-(4-methylphenyl)ethyl]benzene Structure

1-chloro-4-[2-(...

(4-Methylbenzyl)(triphenyl)phosphonium bromide Structure

(4-Methylbenzyl...

~%

1-chloro-4-[2-(4-methylphenyl)ethyl]benzene Structure

1-chloro-4-[2-(...

4-Methylbenzyl bromide Structure

4-Methylbenzyl ...

~%

1-chloro-4-[2-(4-methylphenyl)ethyl]benzene Structure

1-chloro-4-[2-(...

Benzene, 1-methyl-4-(2-phenylethyl)- Structure

Benzene, 1-meth...

~%

1-(4-methylphenyl)-2-phenylethanol Structure

1-(4-methylphen...

(4-phenethylphenyl)methanol Structure

(4-phenethylphe...

p-Tolualdehyde Structure

Detail

1,2-di(p-tolyl)ethane Structure

1,2-di(p-tolyl)...

~%

N-[2-(4-methylphenyl)-1-phenylethyl]acetamide Structure

N-[2-(4-methylp...

4-Methylbenzyl bromide Structure

4-Methylbenzyl ...

~%

N-[2-(4-methylphenyl)-1-phenylethyl]acetamide Structure

N-[2-(4-methylp...

1-Methyl-4-((E)-styryl)-benzene Structure

1-Methyl-4-((E)...

~%

N-[2-(4-methylphenyl)-1-phenylethyl]acetamide Structure

N-[2-(4-methylp...

1-(4-methylphenyl)-2-phenylethanol Structure

1-(4-methylphen...

~%

N-[2-(4-methylphenyl)-1-phenylethyl]acetamide Structure

N-[2-(4-methylp...

p-Tolualdehyde Structure

~%

N-[2-(4-methylphenyl)-1-phenylethyl]acetamide Structure

N-[2-(4-methylp...

Benzene, 1-methyl-4-(2-phenylethyl)- Structure

Benzene, 1-meth...

~%

p-tolylmethanol Structure

p-tolylmethanol

1-(4-methylphenyl)-2-phenylethanol Structure

1-(4-methylphen...

α-Phenyl-4-methylbenzeneethanol Structure

α-Phenyl-4-meth...

Detail

Acetone Structure

Toluene Structure

~%

4-methylphenylacetone Structure

4-methylphenyla...

Benzyl acetate Structure

Detail

Bibenzyl Structure

~%

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

Phenol,4-(2-phenylethenyl)- Structure

Phenol,4-(2-phe...

~%

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

4-Phenethylphenol Structure

4-Phenethylphenol

Dimethyl sulfate Structure

Dimethyl sulfate

~%

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

Bibenzyl Structure

~%

Benzyl alcohol Structure

4-Phenethylphenol Structure

4-Phenethylphenol

~%

Benzyl alcohol Structure

Phenol,4-(2-phenylethenyl)- Structure

Phenol,4-(2-phe...

~%

Benzyl alcohol Structure

Bibenzyl Structure

~%

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Benzaldehyde Structure

Detail

Bibenzyl Structure

~%

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Detail

Toluene Structure

~%

Benzaldehyde Structure

m-Cresol Structure

o-cresol Structure

Detail

Toluene Structure

~%

p-Cresol Structure

Benzaldehyde Structure

m-Cresol Structure

Detail

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

~%

1-(4-methoxyphenyl)-2-phenyl-ethanol Structure

1-(4-methoxyphe...

Benzaldehyde Structure

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

Detail

Bibenzyl Structure

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Toluene Structure

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

4-Phenethylphenol Structure

4-Phenethylphenol

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Phenol,4-(2-phenylethenyl)- Structure

Phenol,4-(2-phe...

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Benzene,1-methoxy-4-(2-phenylethyl)- Structure

Benzene,1-metho...

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Bibenzyl Structure

~%

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Detail

Benzaldehyde Structure

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

Acetonitrile Structure

~%

Acetamide,N-(1,2-diphenylethyl)- Structure

Acetamide,N-(1,...

Bibenzyl Structure

~%

2-(2-phenylethyl)phenol Structure

2-(2-phenylethy...

(S)-(+)-1,2-DIPHENYLETHANOL Structure

(S)-(+)-1,2-DIP...

4-Phenethylphenol Structure

4-Phenethylphenol

Detail

1-chloro-4-[2-(4-methylphenyl)ethyl]benzene Structure

1-chloro-4-[2-(...

~%

4-[2-(4-methylphenyl)ethyl]benzoic acid Structure

4-[2-(4-methylp...

(4-Methylbenzyl)(triphenyl)phosphonium bromide Structure

(4-Methylbenzyl...

~%

4-[2-(4-methylphenyl)ethyl]benzoic acid Structure

4-[2-(4-methylp...

(Z)-1-(4-chlorophenyl)-2-(4-methylphenyl)ethene Structure

(Z)-1-(4-chloro...

~%

4-[2-(4-methylphenyl)ethyl]benzoic acid Structure

4-[2-(4-methylp...

4-Methylbenzyl bromide Structure

4-Methylbenzyl ...

~%

4-[2-(4-methylphenyl)ethyl]benzoic acid Structure

4-[2-(4-methylp...

Regioselectivity of the Rhodium??Catalyzed Hydroboration of ...

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Cu (acac) 2-Catalyzed Synthesis of Functionalized Bis (arylm...

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1, 2??Diarylethanols by Alternative Regioselective Reductive...

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Silver catalyzed zinc Barbier reaction of benzylic halides i...

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