A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents

A Spaggiari, D Vaccari, P Davoli…

Index: Spaggiari, Alberto; Vaccari, Daniele; Davoli, Paolo; Torre, Giovanni; Prati, Fabio Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 2216 - 2219

Full Text: HTML

Citation Number: 61

Abstract

A new application of (PhO) 3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.

 Related Synthetic Route
4-Heptanone, oxime Structure

1188-63-2

4-Heptanone, oxime

~86%

4,4-dichloroheptane Structure

89796-76-9

4,4-dichloroheptane

4-Heptanone Structure

123-19-3

4-Heptanone

~%

4,4-dichloroheptane Structure

89796-76-9

4,4-dichloroheptane

4-chlorohept-3-ene Structure

62748-38-3

4-chlorohept-3-ene

N/A Structure

21370-56-9

N/A

2-Methylcyclohexanone Structure

583-60-8

2-Methylcyclohe...

~%

1-bromo-6-methylcyclohexene Structure

40648-09-7

1-bromo-6-methy...

1-bromo-2-methylcyclohexene Structure

99747-75-8

1-bromo-2-methy...

Pinacolone Structure

75-97-8

Pinacolone

~%

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

33693-77-5

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

2-Methylcyclohexanone Structure

583-60-8

2-Methylcyclohe...

~%

1-bromo-6-methylcyclohexene Structure

40648-09-7

1-bromo-6-methy...

1-bromo-2-methylcyclohexene Structure

99747-75-8

1-bromo-2-methy...

Octanal Structure

124-13-0

Octanal

~77%

1,1-dichlorooctane Structure

20395-24-8

1,1-dichlorooctane

Benzophenone Structure

119-61-9

Benzophenone

~93%

dichlorodiphenylmethane Structure

2051-90-3

dichlorodipheny...

2-Methylcyclohexanone Structure

583-60-8

2-Methylcyclohe...

~%

1-Chloro-2-methyl-1-cyclohexene Structure

16642-49-2

1-Chloro-2-meth...

1-Chloro-6-methyl-1-cyclohexene Structure

16642-50-5

1-Chloro-6-meth...

trans-4-phenylbut-3-en-2-one Structure

1896-62-4

trans-4-phenylb...

~96%

3-bromobuta-1,3-dienylbenzene Structure

489461-62-3

3-bromobuta-1,3...

1,1-dibromo-2-phenylethane Structure

2612-38-6

1,1-dibromo-2-p...

~97%

Benzene, [(1E)-2-bromoethenyl]- Structure

588-72-7

Benzene, [(1E)-...

Phenylacetaldehyde Structure

122-78-1

Phenylacetaldehyde

~%

Benzene, [(1E)-2-bromoethenyl]- Structure

588-72-7

Benzene, [(1E)-...

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

529-34-0

3,4-Dihydronaph...

~92%

4-chloro-1,2-dihydronaphthalene Structure

76181-40-3

4-chloro-1,2-di...

piperonal Structure

120-57-0

piperonal

~95%

5-(dichloromethyl)-1,3-benzodioxole Structure

10584-67-5

5-(dichlorometh...

2-Methylcyclohexanone Structure

583-60-8

2-Methylcyclohe...

~%

1-Chloro-2-methyl-1-cyclohexene Structure

16642-49-2

1-Chloro-2-meth...

1-Chloro-6-methyl-1-cyclohexene Structure

16642-50-5

1-Chloro-6-meth...

4-Heptanone Structure

123-19-3

4-Heptanone

~%

4,4-dichloroheptane Structure

89796-76-9

4,4-dichloroheptane

4-chlorohept-3-ene Structure

62748-38-3

4-chlorohept-3-ene

N/A Structure

21370-56-9

N/A

4-Heptanone Structure

123-19-3

4-Heptanone

~%

4-chlorohept-3-ene Structure

62748-38-3

4-chlorohept-3-ene

N/A Structure

21370-56-9

N/A


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved