Acylation of aromatic substrates with ketenes. An example of vinyl oxocation reactivity

KR Fountain, P Heinze, M Sherwood…

Index: Fountain, K.R.; Heinze, Pamela; Sherwood, Mark; Maddex, Dave; Gerhardt, Greg Canadian Journal of Chemistry, 1980 , vol. 58, p. 1198 - 1205

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Citation Number: 5

Abstract

Acylations of aromatic substrates with ketenes involve the reactivity of species similar to vinyl cations. Resonance stabilization of ketene-aluminum chloride complexes seems to make these complexes less reactive than corresponding vinyl cations. The kinetic isotope effect of the reaction with dimethylketene and benzene is 1.06, compatible with vinylcation cases, but not with acylation with CH3COBF4 types of electrophiles. Substrate specificity was ...

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Anisole Structure

100-66-3

Anisole

2-Methylpropanoyl chloride Structure

79-30-1

2-Methylpropano...

~%

1-propanone, 1-(4-methoxyphenyl)-2-methyl- Structure

2040-20-2

1-propanone, 1-...

1-(2-Methoxyphenyl)-2-methylpropan-1-one Structure

74786-53-1

1-(2-Methoxyphe...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

Anisole Structure

100-66-3

Anisole

~%

1-propanone, 1-(4-methoxyphenyl)-2-methyl- Structure

2040-20-2

1-propanone, 1-...

1-(2-Methoxyphenyl)-2-methylpropan-1-one Structure

74786-53-1

1-(2-Methoxyphe...

DIPHENYLKETENE Structure

525-06-4

DIPHENYLKETENE

Toluene Structure

108-88-3

Toluene

~11%

1-(4-methylphenyl)-2,2-diphenylethanone Structure

41993-27-5

1-(4-methylphen...

2-bromo-2,2-diphenylacetyl chloride Structure

17397-37-4

2-bromo-2,2-dip...

~%

1-(4-methylphenyl)-2,2-diphenylethanone Structure

41993-27-5

1-(4-methylphen...

ether Structure

100-41-4

ether

2-Methylpropanoyl chloride Structure

79-30-1

2-Methylpropano...

~%

1-(4-ETHYL-PHENYL)-2-METHYL-PROPAN-1-ONE Structure

68857-86-3

1-(4-ETHYL-PHEN...

2'-ETHYL-2-METHYLPROPIOPHENONE Structure

99632-24-3

2'-ETHYL-2-METH...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

ether Structure

100-41-4

ether

~%

1-(4-ETHYL-PHENYL)-2-METHYL-PROPAN-1-ONE Structure

68857-86-3

1-(4-ETHYL-PHEN...

DIPHENYLKETENE Structure

525-06-4

DIPHENYLKETENE

benzene Structure

71-43-2

benzene

~%

Ethanone,1,2,2-triphenyl- Structure

1733-63-7

Ethanone,1,2,2-...

2-bromo-2,2-diphenylacetyl chloride Structure

17397-37-4

2-bromo-2,2-dip...

~%

Ethanone,1,2,2-triphenyl- Structure

1733-63-7

Ethanone,1,2,2-...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

2-Methylanisole Structure

578-58-5

2-Methylanisole

~%

1-(4-methoxy-3-methylphenyl)-2-methylpropan-1-one Structure

2954-63-4

1-(4-methoxy-3-...

2-Methylpropanoyl chloride Structure

79-30-1

2-Methylpropano...

Toluene Structure

108-88-3

Toluene

~%

2,4'-dimethylpropiophenone Structure

50390-51-7

2,4'-dimethylpr...

2-Methyl-1-(o-tolyl)propan-1-one Structure

2040-21-3

2-Methyl-1-(o-t...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

Toluene Structure

108-88-3

Toluene

~28%

2,4'-dimethylpropiophenone Structure

50390-51-7

2,4'-dimethylpr...

2-Methylpropanoyl chloride Structure

79-30-1

2-Methylpropano...

Toluene Structure

108-88-3

Toluene

~%

2,4'-dimethylpropiophenone Structure

50390-51-7

2,4'-dimethylpr...

2-Methyl-1-(o-tolyl)propan-1-one Structure

2040-21-3

2-Methyl-1-(o-t...

Anisole Structure

100-66-3

Anisole

DIPHENYLKETENE Structure

525-06-4

DIPHENYLKETENE

~59%

1-(4-methoxyphenyl)-2,2-diphenyl-ethanone Structure

1889-74-3

1-(4-methoxyphe...

2-bromo-2,2-diphenylacetyl chloride Structure

17397-37-4

2-bromo-2,2-dip...

~%

1-(4-methoxyphenyl)-2,2-diphenyl-ethanone Structure

1889-74-3

1-(4-methoxyphe...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

benzene Structure

71-43-2

benzene

~5%

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

Cumene Structure

98-82-8

Cumene

2-Methylpropanoyl chloride Structure

79-30-1

2-Methylpropano...

~%

2-(4-ISOBUTYRYLPHENYL)PROPANE Structure

72846-62-9

2-(4-ISOBUTYRYL...

DIMETHYLKETENE Structure

598-26-5

DIMETHYLKETENE

Cumene Structure

98-82-8

Cumene

~%

2-(4-ISOBUTYRYLPHENYL)PROPANE Structure

72846-62-9

2-(4-ISOBUTYRYL...


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