Hydroxylamine-O-sulfonic acid

It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.

[6] The sulfonation of hydroxylamine can also be effected with chlorosulfonic acid[3] by a method first published in 1925[7] and refined for Organic Syntheses.

[21] Under basic conditions in the presence of primary amines, hydroxylamine-O-sulfonic acid forms with aldehydes and ketones (e.g. cyclohexanone[22]) diaziridines, which can easily be oxidized to the more stable diazirines.

The reaction also provides substituted aziridines from simple aldehydes and ketones with high yield and diastereoselectivity.

[23] 1,2-Benzisoxazole is efficiently produced by nucleophilic attack of hydroxylamine-O-sulfonic acid to the carbonyl group of 2-hydroxybenzaldehyde followed by cyclization.

In a one-pot reaction, N-aryl[3,4-d]pyrazolopyrimidines are obtained in good yields from simple 4,6-dichloropyrimidine-5-carboxaldehyde,[25] which can be used as purine analogs for a wide range of diagnostic and therapeutic applications.

Reaktivität of Hydroxylamine-O-sulfonsäure als Elektrophil und als Nukleophil
Reaktivität of Hydroxylamine- O -sulfonsäure als Elektrophil und als Nukleophil
Synthesis of N-Aminopiperidin with HOSA
Synthesis of N -Aminopiperidin with HOSA
Synthesis of 1-Aminopyridin with HOSA
Synthesis of 1-Aminopyridin with HOSA
Synthesis of 1,2-Diazepinen aus Iminopyridiniumyliden
Synthesis of 1,2-Diazepinen aus Iminopyridiniumyliden
Synthesis of Benzyne and Biphenylene from 1-Aminobenzotriazole
Synthesis of Benzyne and Biphenylene from 1-Aminobenzotriazole
1-Aminotetrazol und 2-Aminotetrazol durch Aminierung of Tetrazol with HOSA
1-Aminotetrazol und 2-Aminotetrazol durch Aminierung of Tetrazol with HOSA
Synthesis of Sulfiminen with HOSA
Synthesis of Sulfiminen with HOSA
Synthesis of primären Sulfonamiden aus Sulfinaten
Synthesis of primären Sulfonamiden aus Sulfinaten
Reaktion of HOSA with Carbonylverbindungen
Reaktion of HOSA with Carbonylverbindungen
2-Azacyclooctanon durch Reaktion of Cycloheptanon with HOSA
2-Azacyclooctanon durch Reaktion of Cycloheptanon with HOSA
3,3-Pentamethylendiaziridin durch Reaktion of Cyclohexanon mit HOSA
3,3-Pentamethylendiaziridin durch Reaktion of Cyclohexanon mit HOSA
Synthesis of Diaziridinen with HOSA
Synthesis of Diaziridinen with HOSA
Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
N-Aryl-Pyrazolopyrimidine
N -Aryl-Pyrazolopyrimidine