Reaktionen der Trialkylsilyl??trifluormethansulfonate, I. Synthese von Trialkylsilyl??Enolethern

…, A Götz, K Hofmann, G Simchen

Index: Emde, Herbert; Goetz, Andreas; Hofmann, Karin; Simchen, Gerhard Liebigs Annalen der Chemie, 1981 , # 9 p. 1643 - 1657

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Citation Number: 1

Abstract

Abstract Die Ketone 2, 2-Bromketone 6, α, β-ungesättigte Ketone 8, 1, 2-Diketone 10 und aliphatische Aldehyde 20 setzen sich mit Trialkyisilyl-triflaten 1 in Gegenwart von Triethylamin (4) bei Raum-temperatur zu den Silylenolethern 3, 7, 9, 11 und 21 um. Die Silylierung unsymmetrischer Ketone 12 mit 1a/4 verläuft mit überschüssigem 1a und 12 regioselektiv im thermodynamischen Sinn zu den Enolethern 13 t. Der Reaktionsablauf ...

 Related Synthetic Route
Octanal Structure

124-13-0

Octanal

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

~57%

trimethyl(oct-1-enoxy)silane Structure

71985-42-7

trimethyl(oct-1...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Isobutyrophenone Structure

611-70-1

Isobutyrophenone

~91%

trimethyl-(2-methyl-1-phenylprop-1-enoxy)silane Structure

39158-85-5

trimethyl-(2-me...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Phenylacetone Structure

103-79-7

Phenylacetone

~%

trimethyl(1-phenylprop-1-en-2-yloxy)silane Structure

43108-63-0

trimethyl(1-phe...

trimethyl(3-phenylprop-1-en-2-yloxy)silane Structure

59021-31-7

trimethyl(3-phe...

Isophorone Structure

78-59-1

Isophorone

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

~%

trimethyl-(3,3,5-trimethylcyclohexa-1,5-dien-1-yl)oxysilane Structure

54781-28-1

trimethyl-(3,3,...

(5,5-dimethyl-3-methylidenecyclohexen-1-yl)oxy-trimethylsilane Structure

80239-27-6

(5,5-dimethyl-3...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

butane-2,3-dione Structure

431-03-8

butane-2,3-dione

~61%

trimethyl(3-trimethylsilyloxybuta-1,3-dien-2-yloxy)silane Structure

31411-71-9

trimethyl(3-tri...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Ethanone,1-(1-cyclohexen-1-yl)- Structure

932-66-1

Ethanone,1-(1-c...

~79%

1-(cyclohexen-1-yl)ethenoxy-trimethylsilane Structure

54781-35-0

1-(cyclohexen-1...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Isobutyraldehyde Structure

78-84-2

Isobutyraldehyde

~49%

Silane, trimethyl((2-methyl-1-propenyl)oxy)- Structure

6651-34-9

Silane, trimeth...

Triethylsilyl trifluoromethanesulfonate Structure

79271-56-0

Triethylsilyl t...

2,4-dimethyl-3-pentanone Structure

565-80-0

2,4-dimethyl-3-...

~85%

2,4-dimethylpent-2-en-3-yloxy(triethyl)silane Structure

80239-20-9

2,4-dimethylpen...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Propionaldehyde Structure

123-38-6

Propionaldehyde

~42%

trimethyl(prop-1-enoxy)silane Structure

50300-18-0

trimethyl(prop-...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

2,4-dimethyl-3-pentanone Structure

565-80-0

2,4-dimethyl-3-...

~66%

2,4-dimethylpent-2-en-3-yloxy(trimethyl)silane Structure

55339-64-5

2,4-dimethylpen...

Isophorone Structure

78-59-1

Isophorone

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

~%

trimethyl-(3,3,5-trimethylcyclohexa-1,5-dien-1-yl)oxysilane Structure

54781-28-1

trimethyl-(3,3,...

(5,5-dimethyl-3-methylidenecyclohexen-1-yl)oxy-trimethylsilane Structure

80239-27-6

(5,5-dimethyl-3...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

4-Methyl-2-pentanone Structure

108-10-1

4-Methyl-2-pentanone

~%

4-Methyl-2-(trimethylsiloxy)-2-penten Structure

2346-32-9

4-Methyl-2-(tri...

trimethyl(4-methylpent-1-en-2-yloxy)silane Structure

59417-87-7

trimethyl(4-met...

Pinacolone Structure

75-97-8

Pinacolone

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

~87%

[(3,3-Dimethyl-1-buten-2-yl)oxy](trimethyl)silane Structure

17510-46-2

[(3,3-Dimethyl-...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

2-Methylcyclohexanone Structure

583-60-8

2-Methylcyclohe...

~%

trimethyl-(2-methylcyclohexen-1-yl)oxysilane Structure

19980-35-9

trimethyl-(2-me...

N/A Structure

19980-33-7

N/A

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Acetophenone Structure

98-86-2

Acetophenone

~81%

1-phenyl(trimethylsiloxy)ethylene Structure

13735-81-4

1-phenyl(trimet...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

1,2-Cyclohexanedione Structure

765-87-7

1,2-Cyclohexanedione

~68%

1,3-Cyclohexadiene, 2,3-bis[(trimethylsilyl)oxy]- Structure

59733-54-9

1,3-Cyclohexadi...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

2-Butanone Structure

78-93-3

2-Butanone

~%

trimethyl[(1-methylpropenyl)oxy]-silane Structure

6651-39-4

trimethyl[(1-me...

but-1-en-2-yloxy(trimethyl)silane Structure

6651-40-7

but-1-en-2-ylox...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Phenylacetone Structure

103-79-7

Phenylacetone

~%

trimethyl(1-phenylprop-1-en-2-yloxy)silane Structure

43108-63-0

trimethyl(1-phe...

trimethyl(3-phenylprop-1-en-2-yloxy)silane Structure

59021-31-7

trimethyl(3-phe...

Trimethylsilyl trifluoromethanesulfonate Structure

27607-77-8

Trimethylsilyl ...

Methyl vinyl ketone Structure

78-94-4

Methyl vinyl ketone

~93%

2-Trimethylsilyloxy-1,3-butadiene Structure

38053-91-7

2-Trimethylsily...


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