NaIO 4/LiBr-mediated aziridination of olefins using chloramine-T

…, PV Chouthaiwale, TM Shaikh, G Suryavanshi…

Index: Karabal, Pratibha U.; Chouthaiwale, Pandurang V.; Shaikh, Tanveer M.; Suryavanshi, Gurunath; Sudalai, Arumugam Tetrahedron Letters, 2010 , vol. 51, # 49 p. 6460 - 6462

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Citation Number: 6

Abstract

A new milder protocol for aziridination of a variety of olefins has been described. The process employs catalytic amount of sodium metaperiodate (NaIO4) as an oxidant and LiBr and chloramine-T as the bromine and nitrogen sources, respectively. Interestingly, the ...

 Related Synthetic Route
Allylbenzene Structure

300-57-2

Allylbenzene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-benzyl-1-(4-methylphenyl)sulfonylaziridine Structure

71535-50-7

2-benzyl-1-(4-m...

4-Chlorostyrene Structure

1073-67-2

4-Chlorostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-93-9

2-(4-chlorophen...

4-Fluorostyrene Structure

405-99-2

4-Fluorostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-fluorophenyl)-1-(toluene-4-sulfonyl)aziridine Structure

250260-25-4

2-(4-fluorophen...

2-Chlorostyrene Structure

2039-87-4

2-Chlorostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

N-(4-tolylsulfonyl)-2-(2-chlorophenyl)aziridine Structure

1227184-73-7

N-(4-tolylsulfo...

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

4-Bromostyrene Structure

2039-82-9

4-Bromostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-bromophenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-95-1

2-(4-bromopheny...

octene Structure

111-66-0

octene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-hexyl-1-(4-methylphenyl)sulfonylaziridine Structure

148961-16-4

2-hexyl-1-(4-me...

stilbene Structure

588-59-0

stilbene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

1-(p-Tolylsulfonyl)-2,3-diphenylaziridine Structure

147054-74-8

1-(p-Tolylsulfo...

Chloramine-T Structure

127-65-1

Chloramine-T

allyl bromide Structure

106-95-6

allyl bromide

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(bromomethyl)-1-(4-methylbenzenesulfonyl)aziridine Structure

244088-62-8

2-(bromomethyl)...

Chloramine-T Structure

127-65-1

Chloramine-T

Cyclohexene Structure

110-83-8

Cyclohexene

~0%

7-Azabicyclo[4.1.0]heptane, 7-[(4-Methylphenyl)sulfonyl]- Structure

68820-12-2

7-Azabicyclo[4....

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

Chloramine-T Structure

127-65-1

Chloramine-T

Indene Structure

95-13-6

Indene

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

N/A Structure

147127-09-1

N/A

Chloramine-T Structure

127-65-1

Chloramine-T

Cyclooctene Structure

931-88-4

Cyclooctene

~0%

9-​Azabicyclo[6.1.0]​nonane, 9-​[(4-​methylphenyl)​sulfonyl]​-​, (1R,​8S)​-​rel Structure

146041-79-4

9-​Azabicyclo[6...

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

4-Methylstyrene Structure

622-97-9

4-Methylstyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-methylphenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-87-1

2-(4-methylphen...

phenylene-ethylene Structure

292638-84-7

phenylene-ethylene

Chloramine-T Structure

127-65-1

Chloramine-T

~0%

1-[(4-Methylphenyl)sulfonyl]-2-phenylaziridine Structure

24395-14-0

1-[(4-Methylphe...

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

Chloramine-T Structure

127-65-1

Chloramine-T

Cyclohexene Structure

110-83-8

Cyclohexene

~58%

7-Azabicyclo[4.1.0]heptane, 7-[(4-Methylphenyl)sulfonyl]- Structure

68820-12-2

7-Azabicyclo[4....

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

4-Methylstyrene Structure

622-97-9

4-Methylstyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~39%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-methylphenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-87-1

2-(4-methylphen...

4-Chlorostyrene Structure

1073-67-2

4-Chlorostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~76%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-93-9

2-(4-chlorophen...

4-Bromostyrene Structure

2039-82-9

4-Bromostyrene

Chloramine-T Structure

127-65-1

Chloramine-T

~72%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-(4-bromophenyl)-1-(4-methylphenyl)sulfonylaziridine Structure

97401-95-1

2-(4-bromopheny...

VINYLCYCLOHEXANE Structure

695-12-5

VINYLCYCLOHEXANE

Chloramine-T Structure

127-65-1

Chloramine-T

~59%

N/A Structure

1259328-88-5

N/A

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

Detail
octene Structure

111-66-0

octene

Chloramine-T Structure

127-65-1

Chloramine-T

~58%

4-Toluenesulfonamide Structure

70-55-3

4-Toluenesulfonamide

2-hexyl-1-(4-methylphenyl)sulfonylaziridine Structure

148961-16-4

2-hexyl-1-(4-me...


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