A general procedure for preparing. alpha.-lithiosilanes. Generalization of the Peterson olefination

…, RR Hutchins, BM McHenry, PR Willey

Index: Cohen, Theodore; Sherbine, James P.; Matz, James R.; Hutchins, Robert R.; McHenry, Barry M.; Willey, Paul R. Journal of the American Chemical Society, 1984 , vol. 106, # 11 p. 3245 - 3252

Full Text: HTML

Citation Number: 76

Abstract

Abstract: A particularly convenient method for the preparation of a-lithiosilanes consists of the reductive lithiation of diphenyl thioacetals or thioketals with lithium 1-(dimethylamino) naphthalenide, treatment of the resulting anion with trimethylsilyl chloride, and reductive lithiation, with the same reducing agent, of the resulting a-(pheny1thio) silane. The generality of the procedure is demonstrated by th preparation of a-lithiosilanes in which ...

 Related Synthetic Route
Thiophenol Structure

108-98-5

Thiophenol

4-tert-Butylcyclohexanone Structure

98-53-3

4-tert-Butylcyc...

~81%

(4-tert-butyl-1-phenylsulfanylcyclohexyl)sulfanylbenzene Structure

85895-63-2

(4-tert-butyl-1...

trimethyl(1-phenylsulfanylpropyl)silane Structure

76200-34-5

trimethyl(1-phe...

4-tert-Butylcyclohexanone Structure

98-53-3

4-tert-Butylcyc...

~%

4-tert-butyl-1-(1-trimethylsilylpropyl)cyclohexan-1-ol Structure

89656-93-9

4-tert-butyl-1-...

trimethyl(1-phenylsulfanylpropyl)silane Structure

76200-34-5

trimethyl(1-phe...

ch3cho Structure

75-07-0

ch3cho

~%

3-trimethylsilylpentan-2-ol Structure

89656-94-0

3-trimethylsily...

4-tert-butyl-1-(1-trimethylsilylpropyl)cyclohexan-1-ol Structure

89656-93-9

4-tert-butyl-1-...

~81%

1-tert-butyl-4-propylidenecyclohexane Structure

51197-95-6

1-tert-butyl-4-...

7,7-bis(phenylsulfanyl)bicyclo[4.1.0]heptane Structure

58681-16-6

7,7-bis(phenyls...

~%

7-hexylidenebicyclo[4.1.0]heptane Structure

81236-88-6

7-hexylidenebic...

N/A Structure

115025-76-8

N/A

~%

7-hexylidenebicyclo[4.1.0]heptane Structure

81236-88-6

7-hexylidenebic...

Thiophenol Structure

108-98-5

Thiophenol

~%

[cyclohexyl(phenylsulfanyl)methyl]-trimethylsilane Structure

89656-95-1

[cyclohexyl(phe...

Cyclohexanecarboxaldehyde Structure

2043-61-0

Cyclohexanecarb...

~%

[cyclohexyl(phenylsulfanyl)methyl]-trimethylsilane Structure

89656-95-1

[cyclohexyl(phe...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

[cyclohexyl(phenylsulfanyl)methyl]sulfanylbenzene Structure

54905-14-5

[cyclohexyl(phe...

~%

[cyclohexyl(phenylsulfanyl)methyl]-trimethylsilane Structure

89656-95-1

[cyclohexyl(phe...

Thiophenol Structure

108-98-5

Thiophenol

~%

trimethyl(2-phenylsulfanylpropan-2-yl)silane Structure

89656-96-2

trimethyl(2-phe...

(4-methoxyphenyl)(1-(trimethylsilyl)cyclopropyl)methanol Structure

89657-04-5

(4-methoxypheny...

~87%

1-(cyclopropylidenemethyl)-4-methoxybenzene Structure

55088-84-1

1-(cyclopropyli...

Thiophenol Structure

108-98-5

Thiophenol

~%

trimethyl(1-phenylsulfanylpropyl)silane Structure

76200-34-5

trimethyl(1-phe...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

1,1-di(phenylsulfanyl)propane Structure

15486-58-5

1,1-di(phenylsu...

~%

trimethyl(1-phenylsulfanylpropyl)silane Structure

76200-34-5

trimethyl(1-phe...

1-cyclohexyl-2-methyl-2-(trimethylsilyl)propan-1-ol Structure

89656-97-3

1-cyclohexyl-2-...

~92%

2-methylprop-1-enylcyclohexane Structure

89656-98-4

2-methylprop-1-...

Cyclohexanone Structure

108-94-1

Cyclohexanone

~%

trimethyl-(1-phenylsulfanylcyclohexyl)silane Structure

89656-99-5

trimethyl-(1-ph...

Thiophenol Structure

108-98-5

Thiophenol

~%

trimethyl-(1-phenylsulfanylcyclohexyl)silane Structure

89656-99-5

trimethyl-(1-ph...

(4-(tert-butyl)-1-(trimethylsilyl)cyclohexyl)(cyclohexyl)methanol Structure

89657-02-3

(4-(tert-butyl)...

~89%

1-tert-butyl-4-(cyclohexylmethylidene)cyclohexane Structure

89657-03-4

1-tert-butyl-4-...

(4-tert-butyl-1-phenylsulfanylcyclohexyl)sulfanylbenzene Structure

85895-63-2

(4-tert-butyl-1...

~%

1-tert-butyl-4-(cyclohexylmethylidene)cyclohexane Structure

89657-03-4

1-tert-butyl-4-...

4-tert-Butylcyclohexanone Structure

98-53-3

4-tert-Butylcyc...

~%

1-tert-butyl-4-(cyclohexylmethylidene)cyclohexane Structure

89657-03-4

1-tert-butyl-4-...

trans-1-(phenylthio)-1-(trimethylsilyl)-4-tert-butylcyclohexane Structure

89657-01-2

trans-1-(phenyl...

~%

1-tert-butyl-4-(cyclohexylmethylidene)cyclohexane Structure

89657-03-4

1-tert-butyl-4-...

1-(TRIMETHYLSILYL)CYCLOPROPYL PHENYL SULFIDE Structure

74379-74-1

1-(TRIMETHYLSIL...

4-tert-Butylcyclohexanone Structure

98-53-3

4-tert-Butylcyc...

~%

4-tert-butyl-1-(1-trimethylsilylcyclopropyl)cyclohexan-1-ol Structure

89657-06-7

4-tert-butyl-1-...

Chlorotrimethylsilane Structure

75-77-4

Chlorotrimethyl...

(1-phenylsulfanylcyclopropyl)sulfanylbenzene Structure

69519-84-2

(1-phenylsulfan...

~%

1-(TRIMETHYLSILYL)CYCLOPROPYL PHENYL SULFIDE Structure

74379-74-1

1-(TRIMETHYLSIL...

4-tert-butyl-1-(1-trimethylsilylcyclopropyl)cyclohexan-1-ol Structure

89657-06-7

4-tert-butyl-1-...

~83%

1-tert-butyl-4-cyclopropylidenecyclohexane Structure

89657-07-8

1-tert-butyl-4-...

7,7-bis(phenylsulfanyl)bicyclo[4.1.0]heptane Structure

58681-16-6

7,7-bis(phenyls...

~%

7-(2-methylprop-2-enylidene)bicyclo[4.1.0]heptane Structure

89657-10-3

7-(2-methylprop...

N/A Structure

115025-76-8

N/A

~%

7-(2-methylprop-2-enylidene)bicyclo[4.1.0]heptane Structure

89657-10-3

7-(2-methylprop...

2-propenyl(7-(trimethylsilyl)bicyclo(4.1.0)hept-7-yl)methanol Structure

89675-83-2

2-propenyl(7-(t...

~99%

7-(2-methylprop-2-enylidene)bicyclo[4.1.0]heptane Structure

89657-10-3

7-(2-methylprop...

2-propenyl(6-(trimethylsilyl)bicyclo(3.1.0)hex-6-yl)methanol Structure

89657-13-6

2-propenyl(6-(t...

~92%

6-(2-methylprop-2-enylidene)bicyclo[3.1.0]hexane Structure

89657-14-7

6-(2-methylprop...

6-(phenylthio)-6-(trimethylsilyl)bicyclo[3.1.0]hexane Structure

115025-77-9

6-(phenylthio)-...

~%

6-(2-methylprop-2-enylidene)bicyclo[3.1.0]hexane Structure

89657-14-7

6-(2-methylprop...

6,6-bis(phenylsulfanyl)bicyclo[3.1.0]hexane Structure

83711-04-0

6,6-bis(phenyls...

~%

6-(2-methylprop-2-enylidene)bicyclo[3.1.0]hexane Structure

89657-14-7

6-(2-methylprop...

[2-(2-methylprop-1-enyl)-1-phenylsulfanylcyclopropyl]sulfanylbenzene Structure

71987-46-7

[2-(2-methylpro...

~%

1-methoxy-4-[[2-(2-methylprop-1-enyl)cyclopropylidene]methyl]benzene Structure

89657-18-1

1-methoxy-4-[[2...

2-(2-methyl-1-propenyl)-1-(phenylthio)-1-(trimethylsilyl)cyclopropane Structure

345621-97-8

2-(2-methyl-1-p...

~%

1-methoxy-4-[[2-(2-methylprop-1-enyl)cyclopropylidene]methyl]benzene Structure

89657-18-1

1-methoxy-4-[[2...


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