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

The Journal of Organic Chemistry

Surface-Mediated Reactions. 4. Hydrohalogenation of Alkynes

PJ Kropp, SD Crawford

Index: Kropp, Paul J.; Crawford, Scott D. Journal of Organic Chemistry, 1994 , vol. 59, # 11 p. 3102 - 3112

Full Text: HTML

Citation Number: 68

Abstract

The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (I), which underwent no reaction in CHzClz solution ...

Hept-1-yne Structure

~1%

2,2-dichloroheptane Structure

2,2-dichloroheptane

2-chlorohept-1-ene Structure

2-chlorohept-1-ene

(Z)-2-Chloro-2-heptene Structure

(Z)-2-Chloro-2-...

Detail

3,3-Dimethyl-1-Butyne Structure

3,3-Dimethyl-1-...

~%

3,3-dimethyl-1-phenylbutan-1-one Structure

3,3-dimethyl-1-...

(3,3,3-TRIFLUOROPROPYL)METHYLDIMETHOXYSILANE Structure

(3,3,3-TRIFLUOR...

~18%

3,3-dimethyl-1-phenylbutan-1-one Structure

3,3-dimethyl-1-...

N/A Structure

(3,3,3-TRIFLUOROPROPYL)METHYLDIMETHOXYSILANE Structure

(3,3,3-TRIFLUOR...

~%

N/A Structure

(Z)-(1-Chloro-3,3-dimethyl-1-butenyl)benzene Structure

(Z)-(1-Chloro-3...

3,3-dimethyl-1-phenylbutan-1-one Structure

3,3-dimethyl-1-...

(3,3,3-TRIFLUOROPROPYL)METHYLDIMETHOXYSILANE Structure

(3,3,3-TRIFLUOR...

~%

3,3-dimethyl-1-phenylbutan-1-one Structure

3,3-dimethyl-1-...

(E)-(1-Bromo-3,3-dimethyl-1-butenyl)benzene Structure

(E)-(1-Bromo-3,...

(Z)-(1-Bromo-3,3-dimethyl-1-butenyl)benzene Structure

(Z)-(1-Bromo-3,...

(3,3,3-TRIFLUOROPROPYL)METHYLDIMETHOXYSILANE Structure

(3,3,3-TRIFLUOR...

~%

3,3-dimethyl-1-phenylbutan-1-one Structure

3,3-dimethyl-1-...

N/A Structure

N/A Structure

phenylpropyne Structure

~64%

1-bromoprop-1-enylbenzene Structure

1-bromoprop-1-e...

3,3-Dimethyl-1-Butyne Structure

3,3-Dimethyl-1-...

~%

3,3-Dibromo-2,2-dimethylbutane Structure

3,3-Dibromo-2,2...

2,3-dibromo-2,3-dimethylbutane Structure

2,3-dibromo-2,3...

3,3-Dimethyl-1-Butyne Structure

3,3-Dimethyl-1-...

~%

Pinacolone Structure

2-bromo-3,3-dimethylbut-1-ene Structure

2-bromo-3,3-dim...

4-Octyne Structure

~%

4-iodooct-4-ene Structure

4-iodooct-4-ene

(Z)-4-iodo-4-octene Structure

(Z)-4-iodo-4-octene

Diphenylacetylene Structure

Diphenylacetylene

~%

Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis- Structure

Benzene,1,1'-[(...

Diphenylacetylene Structure

Diphenylacetylene

~%

(E)-1,2-Diphenyl-1-chloroethene Structure

(E)-1,2-Dipheny...

Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis- Structure

Benzene,1,1'-[(...

(E)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene Structure

(E)-1,1'-(1-Iod...

~%

(1-iodo-2-phenylethenyl)benzene Structure

(1-iodo-2-pheny...

Diphenylacetylene Structure

Diphenylacetylene

~%

(1-iodo-2-phenylethenyl)benzene Structure

(1-iodo-2-pheny...

Diphenylacetylene Structure

Diphenylacetylene

~%

2-Phenylacetophenone Structure

2-Phenylacetophenone

(E)-1,1'-(1-Iodo-1,2-ethenediyl)bisbenzene Structure

(E)-1,1'-(1-Iod...

(1-iodo-2-phenylethenyl)benzene Structure

(1-iodo-2-pheny...

2-Heptanone Structure

~%

2,2-dichloroheptane Structure

2,2-dichloroheptane

Hept-1-yne Structure

~52%

2,2-dichloroheptane Structure

2,2-dichloroheptane

2-chlorohept-1-ene Structure

2-chlorohept-1-ene

(Z)-2-Chloro-2-heptene Structure

(Z)-2-Chloro-2-...

Detail

The Chemistry of the Acetylenes. I. The Preparation of 1-Hep...

[Bachman; Hill Journal of the American Chemical Society, 1934 , vol. 56, p. 2730]

The Chemistry of the Acetylenes. I. The Preparation of 1-Hep...

[Bachman; Hill Journal of the American Chemical Society, 1934 , vol. 56, p. 2730]