Silanes in organic synthesis. 8. Preparation of vinylsilanes from ketones and their regiospecific cyclopentenone annulation

LA Paquette, WE Fristad, DS Dime…

Index: Paquette, Leo A.; Fristad, William E.; Dime, David S.; Bailey, Thomas R. Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 3017 - 3028

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Citation Number: 133

Abstract

A general method is described for the formation of vinylsilanes from ketones. Thus, conversion to the benzene-or p-toluenesulfonylhydrazone and sequential treatment with n- butyllithium and chlorotrimethylsilane in anhydrous tetramethylethylenediamine proceeds regiospecifically to afford the less substituted vinylsilane (in unsymmetrical cases). FriedelCrafts acylation with acryloyl chlorides and aluminum chloride and subsequent ...

 Related Synthetic Route
1-Cyclohexenyltrimethylsilane Structure

17874-17-8

1-Cyclohexenylt...

~%

3-METHYL-2,3,4,5,6,7-HEXAHYDRO-1H-INDEN-1-ONE Structure

18631-68-0

3-METHYL-2,3,4,...

N-(cyclohexylideneamino)benzenesulfonamide Structure

61892-19-1

N-(cyclohexylid...

~%

3-METHYL-2,3,4,5,6,7-HEXAHYDRO-1H-INDEN-1-ONE Structure

18631-68-0

3-METHYL-2,3,4,...

2-Heptanone Structure

110-43-0

2-Heptanone

~%

hept-1-en-2-yl(trimethyl)silane Structure

51666-95-6

hept-1-en-2-yl(...

3-methylcrotonoyl chloride Structure

3350-78-5

3-methylcrotono...

cyclopenten-1-yl(trimethyl)silane Structure

14579-07-8

cyclopenten-1-y...

~%

1-(cyclopenten-1-yl)-3-methylbut-2-en-1-one Structure

41414-30-6

1-(cyclopenten-...

cyclopentanone benzenesulfonylhydrazone Structure

66741-06-8

cyclopentanone ...

~%

1-(cyclopenten-1-yl)-3-methylbut-2-en-1-one Structure

41414-30-6

1-(cyclopenten-...

Cyclopentanone Structure

120-92-3

Cyclopentanone

~%

1-(cyclopenten-1-yl)-3-methylbut-2-en-1-one Structure

41414-30-6

1-(cyclopenten-...

1-Cyclohexenyltrimethylsilane Structure

17874-17-8

1-Cyclohexenylt...

Acrylyl chloride Structure

814-68-6

Acrylyl chloride

~12%

2,3,3a,4,5,6-Hexahydro-(1H)-inden-1-one Structure

40954-63-0

2,3,3a,4,5,6-He...

2,3,4,5,6,7-Hexahydro-1H-indene-1-one Structure

22118-00-9

2,3,4,5,6,7-Hex...

(E)-1-(trimethylsilyl)cyclododecene Structure

73839-43-7

(E)-1-(trimethy...

~%

2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-3-methyl-1H-cyclopent-1-ylcyclododecen-1-one Structure

56975-51-0

2,3,4,5,6,7,8,9...

cyclododecanone benzenesulfonylhydrazone Structure

73839-48-2

cyclododecanone...

~%

2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-3-methyl-1H-cyclopent-1-ylcyclododecen-1-one Structure

56975-51-0

2,3,4,5,6,7,8,9...

(E)-1-((E)-cyclododec-1-en-1-yl)but-2-en-1-one Structure

72233-35-3

(E)-1-((E)-cycl...

~%

2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-3-methyl-1H-cyclopent-1-ylcyclododecen-1-one Structure

56975-51-0

2,3,4,5,6,7,8,9...

15-methylbicyclo[10.3.0]pentadec-11-en-13-one Structure

72233-36-4

15-methylbicycl...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

cyclopentanone benzenesulfonylhydrazone Structure

66741-06-8

cyclopentanone ...

~%

cyclopenten-1-yl(trimethyl)silane Structure

14579-07-8

cyclopenten-1-y...

Cyclohexanone Structure

108-94-1

Cyclohexanone

Benzenesulfonohydrazide Structure

80-17-1

Benzenesulfonoh...

~91%

N-(cyclohexylideneamino)benzenesulfonamide Structure

61892-19-1

N-(cyclohexylid...

4-Methylcinnamic acid Structure

1866-39-3

4-Methylcinnami...

~%

TRIMETHYL(P-TOLYLETHYNYL)SILANE Structure

4186-14-5

TRIMETHYL(P-TOL...

(2RS,3SR)-2,3-dibromo-3-(4-methylphenyl)propanoic acid Structure

52916-86-6

(2RS,3SR)-2,3-d...

~%

TRIMETHYL(P-TOLYLETHYNYL)SILANE Structure

4186-14-5

TRIMETHYL(P-TOL...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

(E)-β-bromo-p-methylstyrene Structure

73839-44-8

(E)-β-bromo-p-m...

~%

TRIMETHYL(P-TOLYLETHYNYL)SILANE Structure

4186-14-5

TRIMETHYL(P-TOL...

(E)-trimethyl[2-(4-methylphenyl)ethenyl]silane Structure

73839-45-9

(E)-trimethyl[2...

3,4-Dihydronaphthalen-1(2H)-one Structure

529-34-0

3,4-Dihydronaph...

~%

3,4-dihydronaphthalen-1-yl(trimethyl)silane Structure

61892-23-7

3,4-dihydronaph...

Benzenesulfonohydrazide Structure

80-17-1

Benzenesulfonoh...

6-Methoxytetralone Structure

1078-19-9

6-Methoxytetralone

~67%

(E)-N'-(6-Methoxy-3,4-dihydronaphthalen-1(2H)-ylidene)benzenesulfonohydrazide Structure

66227-85-8

(E)-N'-(6-Metho...


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