Tetrahedron letters

A convenient conversion of primary amines into the corresponding halides—Radical promoted halodeamination via N-substituted-N-Tosylhydrazines

LR Collazo, FS Guziec, WX Hu, R Pankayatselvan

Index: Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi Tetrahedron Letters, 1994 , vol. 35, # 43 p. 7911 - 7914

Full Text: HTML

Citation Number: 7

Abstract

Abstract Treatment of 1-substituted-1-tosylhydrazines with 2 equivalents of NCS or NBS in dry THF in presence of light affords the corresponding alkyl halides in good yields. This reaction presumably involves the initial formation of a stabilized hydrazyl radical which is halogenated in a radical chain process. Elimination of p-toluenesulfinic acid and extrusion of nitrogen leads to the corresponding alkyl halide. This route provides an improved method ...

 Related Synthetic Route
N/A Structure

146404-40-2

N/A

~85%

1-Chlorohexadecane Structure

4860-03-1

1-Chlorohexadecane

Tosyl chloride Structure

98-59-9

Tosyl chloride

Learn More
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine Structure

141666-87-7

1-Tosyl-1-<2-(4...

~0%

p-(2-bromoethyl)anisole Structure

14425-64-0

p-(2-bromoethyl...

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N-(4-chlorophenethyl)-4-methylbenzenesulfonohydrazide Structure

146404-41-3

N-(4-chlorophen...

~0%

1-(2-Bromoethyl)-4-chlorobenzene Structure

6529-53-9

1-(2-Bromoethyl...

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N/A Structure

146404-40-2

N/A

~0%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

1-Bromohexadecane Structure

112-82-3

1-Bromohexadecane

Learn More
Structure

151259-26-6

~0%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

1-Bromododecane Structure

143-15-7

1-Bromododecane

Learn More
1-p-Toluolsulfonyl-1-phenethyl-hydrazin Structure

159690-31-0

1-p-Toluolsulfo...

~0%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

(2-Bromoethyl)benzene Structure

103-63-9

(2-Bromoethyl)b...

Learn More
4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N-dodecyl-4-methyl-Benzenesulfonamide Structure

1635-09-2

N-dodecyl-4-met...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N-Hexadecyl-4-toluenesulfonamide Structure

18049-99-5

N-Hexadecyl-4-t...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N/A Structure

141666-91-3

N/A

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
4-methyl-N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide Structure

141666-92-4

4-methyl-N-[2-(...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
Tosyl chloride Structure

98-59-9

Tosyl chloride

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine Structure

141666-87-7

1-Tosyl-1-<2-(4...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N-(4-chlorophenethyl)-4-methylbenzenesulfonohydrazide Structure

146404-41-3

N-(4-chlorophen...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
N/A Structure

146404-40-2

N/A

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
Structure

151259-26-6

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
1-p-Toluolsulfonyl-1-phenethyl-hydrazin Structure

159690-31-0

1-p-Toluolsulfo...

~%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
4-Methylbenzenesulfinic acid Structure

536-57-2

4-Methylbenzene...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
N-dodecyl-4-methyl-Benzenesulfonamide Structure

1635-09-2

N-dodecyl-4-met...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
N-Hexadecyl-4-toluenesulfonamide Structure

18049-99-5

N-Hexadecyl-4-t...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
N/A Structure

141666-91-3

N/A

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
4-methyl-N-[2-(4-methoxyphenyl)ethyl]benzenesulfonamide Structure

141666-92-4

4-methyl-N-[2-(...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine Structure

141666-87-7

1-Tosyl-1-<2-(4...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
N/A Structure

146404-40-2

N/A

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
1-p-Toluolsulfonyl-1-phenethyl-hydrazin Structure

159690-31-0

1-p-Toluolsulfo...

~68%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

(2-Bromoethyl)benzene Structure

103-63-9

(2-Bromoethyl)b...

Learn More
N-(4-chlorophenethyl)-4-methylbenzenesulfonohydrazide Structure

146404-41-3

N-(4-chlorophen...

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
Structure

151259-26-6

~%

4-Methyl-N-phenethyl-benzenesulfonamide Structure

5450-75-9

4-Methyl-N-phen...

Learn More
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine Structure

141666-87-7

1-Tosyl-1-<2-(4...

~80%

Tosyl chloride Structure

98-59-9

Tosyl chloride

4-(2-Chloroethyl)anisole Structure

18217-00-0

4-(2-Chloroethy...

Learn More
N-(4-chlorophenethyl)-4-methylbenzenesulfonohydrazide Structure

146404-41-3

N-(4-chlorophen...

~84%

1-(2-Bromoethyl)-4-chlorobenzene Structure

6529-53-9

1-(2-Bromoethyl...

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
1-Tosyl-1-<2-(4-methoxyphenyl)ethyl>hydrazine Structure

141666-87-7

1-Tosyl-1-<2-(4...

~86%

p-(2-bromoethyl)anisole Structure

14425-64-0

p-(2-bromoethyl...

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

Learn More
4-Methoxyphenylethylamine Structure

55-81-2

4-Methoxyphenyl...

~%

p-(2-bromoethyl)anisole Structure

14425-64-0

p-(2-bromoethyl...

Learn More
Structure

151259-26-6

~65%

4-methylbenzenesulfonyl bromide Structure

1950-69-2

4-methylbenzene...

1-Bromododecane Structure

143-15-7

1-Bromododecane

Learn More
N-(4-chlorophenethyl)-4-methylbenzenesulfonohydrazide Structure

146404-41-3

N-(4-chlorophen...

~96%

1-Chloro-4-(2-chloroethyl)benzene Structure

32327-70-1

1-Chloro-4-(2-c...

Tosyl chloride Structure

98-59-9

Tosyl chloride

Learn More
1-p-Toluolsulfonyl-1-phenethyl-hydrazin Structure

159690-31-0

1-p-Toluolsulfo...

~58%

(2-Chloroethyl)benzene Structure

622-24-2

(2-Chloroethyl)...

Tosyl chloride Structure

98-59-9

Tosyl chloride

Learn More

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