e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron letters

Methyl group migration in the reactions of alkynyltrialkylborates

A Pelter, RA Drake

Index: Tetrahedron Letters, , vol. 29, # 33 p. 4181 - 4184

Full Text: HTML

Citation Number: 23

Abstract

... JavaScript is disabled on your browser. Please enable JavaScript to use all the features on this page. Tetrahedron Letters. Volume 29, Issue 33, 1988, Pages 4181–4184. Cover image Cover image. Methyl group migration in the reactions of alkynyltrialkylborates. ...

lithium dimethyl(phenyl)(phenylethynyl)borate Structure

lithium dimethy...

~16%

phenylpropyne Structure

Diphenylacetylene Structure

Diphenylacetylene

lithium dimethylbis(phenylethynyl)borate Structure

lithium dimethy...

~64%

phenylpropyne Structure

(iodoethynyl)benzene Structure

(iodoethynyl)benzene

butadiyne, diphenyl- Structure

butadiyne, diphenyl-

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~53%

phenylpropyne Structure

1-Hexyn-1-ylbenzene Structure

1-Hexyn-1-ylbenzene

lithium (4-methoxyphenyl)dimethyl(phenylethynyl)borate Structure

lithium (4-meth...

~38%

phenylpropyne Structure

Anisole, p-(phenylethynyl)- Structure

Anisole, p-(phe...

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~41%

5-Decyne Structure

2-Heptyne Structure

N/A Structure

~82%

phenylpropyne Structure

Phenylacetylene Structure

Phenylacetylene

Phenylacetone Structure

N/A Structure

Dimethyl sulfate Structure

Dimethyl sulfate

~25%

phenylpropyne Structure

2,3-dimethyl-3-phenyl-butanol Structure

2,3-dimethyl-3-...

Detail

N/A Structure

Dimethyl sulfate Structure

Dimethyl sulfate

~%

phenylpropyne Structure

N/A Structure

~8%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

Hex-1-yne Structure

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~12%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~11%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

5-Decanone Structure

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~0%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

dec-5-ene Structure

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~22%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

TRANS-2-HEPTENE Structure

TRANS-2-HEPTENE

dec-5-ene Structure

Detail

N/A Structure

~%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

3-Methyl-2-heptene Structure

3-Methyl-2-heptene

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~0%

1-Phenyl-2-hexanone Structure

1-Phenyl-2-hexanone

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Phenylacetylene Structure

Phenylacetylene

Detail

N/A Structure

~7%

phenylpropyne Structure

Phenylacetylene Structure

Phenylacetylene

Phenylacetone Structure

N/A Structure

~73%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

Hex-1-yne Structure

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

Dimethyl sulfate Structure

Dimethyl sulfate

~66%

6-methyl-decan-5-one Structure

6-methyl-decan-5-one

2-Heptanone, 3-methyl- Structure

2-Heptanone, 3-...

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~55%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~57%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

5-Decanone Structure

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~0%

6-methyl-decan-5-one Structure

6-methyl-decan-5-one

2-Heptanone, 3-methyl- Structure

2-Heptanone, 3-...

Hex-1-yne Structure

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~25%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

dec-5-ene Structure

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~25%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

TRANS-2-HEPTENE Structure

TRANS-2-HEPTENE

dec-5-ene Structure

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

Dimethyl sulfate Structure

Dimethyl sulfate

~47%

6-Methylundec-5-ene Structure

6-Methylundec-5-ene

3-Methyl-2-heptene Structure

3-Methyl-2-heptene

Detail

N/A Structure

~0%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

Hex-1-yne Structure

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~0%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

2-Heptanone Structure

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~0%

2-Heptanol, 2-methyl- Structure

2-Heptanol, 2-m...

5-Methyldecan-5-ol Structure

5-Methyldecan-5-ol

5-Decanone Structure

Detail

N/A Structure

~0%

2-Methyl-1-phenyl-2-propanol Structure

2-Methyl-1-phen...

Phenylacetylene Structure

Phenylacetylene

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~%

β-Methylstyrene Structure

β-Methylstyrene

2-Methyl-1-phenyl-2-propanol Structure

2-Methyl-1-phen...

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Detail

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~11%

1-Phenyl-2-hexanone Structure

1-Phenyl-2-hexanone

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Phenylacetylene Structure

Phenylacetylene

Detail

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~66%

1-Phenyl-2-hexanone Structure

1-Phenyl-2-hexanone

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Phenylacetylene Structure

Phenylacetylene

Detail

N/A Structure

~4%

phenylpropyne Structure

Phenylacetylene Structure

Phenylacetylene

Phenylacetone Structure

N/A Structure

Dimethyl sulfate Structure

Dimethyl sulfate

~5%

phenylpropyne Structure

2,3-dimethyl-3-phenyl-butanol Structure

2,3-dimethyl-3-...

Detail

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~28%

β-Methylstyrene Structure

β-Methylstyrene

[(E)-1-Hexenyl]benzene Structure

[(E)-1-Hexenyl]...

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Detail

N/A Structure

~%

Phenylacetylene Structure

Phenylacetylene

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~%

β-Methylstyrene Structure

β-Methylstyrene

2-Methyl-1-phenyl-2-propanol Structure

2-Methyl-1-phen...

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Detail

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~36%

phenylpropyne Structure

1-Hexyn-1-ylbenzene Structure

1-Hexyn-1-ylbenzene

lithium dimethylbis(phenylethynyl)borate Structure

lithium dimethy...

~13%

phenylpropyne Structure

(iodoethynyl)benzene Structure

(iodoethynyl)benzene

butadiyne, diphenyl- Structure

butadiyne, diphenyl-

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~0%

β-Methylstyrene Structure

β-Methylstyrene

[(E)-1-Hexenyl]benzene Structure

[(E)-1-Hexenyl]...

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Detail

lithium butyldimethyl(phenylethynyl)borate Structure

lithium butyldi...

~%

β-Methylstyrene Structure

β-Methylstyrene

2-Methyl-1-phenyl-2-propanol Structure

2-Methyl-1-phen...

2-methyl-1-phenyl-2-hexanol Structure

2-methyl-1-phen...

Detail

lithium butyl(hex-1-yn-1-yl)dimethylborate Structure

lithium butyl(h...

~50%

5-Decyne Structure

2-Heptyne Structure

N/A Structure

~87%

2-Heptyne Structure

1-Iodo-1-hexyne Structure

1-Iodo-1-hexyne

N/A Structure

Dimethyl sulfate Structure

Dimethyl sulfate

~%

2-Heptyne Structure

Fritsch–Buttenberg–Wiechell rearrangement to alkynes from ge...

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