Azide → 3-Azidomethyl-3-methyloxetane
Reaktionsgleichung
N(C1CCO1)=[N+]=[N-].[N-:8]=[N+:9]=[N-:10].Cl[CH2:12][C:13]1([CH3:17])[CH2:16][O:15][CH2:14]1>>[N:8]([CH2:12][C:13]1([CH3:17])[CH2:16][O:15][CH2:14]1)=[N+:9]=[N-:10]Komponenten
Versuchsvorschrift
As such, it has been discovered that monofunctional azidooxetane compounds, i.e., 3-azidomethyl-3-R1 -oxetanes, can also be prepared by combining a neat halooxetane with an aqueous metallic azide solution and a phase transfer catalyst (PTC). For example, using the process of the present invention, 3-chloromethyl-3-methyloxetane gives the corresponding 3-azidomethyl-3-methyloxetane (AMMO) in 97% yield. Moreover, 3-bromomethyl-3-hydroxymethyloxetane was previously converted to the corresponding 3-azidomethyl-3-hydroxymethyloxetane in acetone. Using the process of the present invention, however, 3-bromomethyl-3-hydroxymethyloxetane is converted to the corresponding 3-azidomethyl-3-hydroxymethyloxetane, without the use of an organic solvent, using an aqueous sodium azide solution and a phase transfer catalyst. The process of the present invention gives the same result with a faster rate of reaction and without the use of an organic solvent. In addition, 3-chloromethyl-3-methyloxetane 3-chloromethyl-3-phenoxymethyloxetane reacts with an aqueous solution of sodium azide in water with a PTC to give 3-azidomethyl-3-phenoxymethyloxetane in 87% yield.
Aufarbeitung
- customcan also be prepared
Quellen und Nachweise
- ORD-Eintrag
- ord-63613d3af50b4ace9d8bd76853e0971a
- Quelldatensatz
- uspto-grants-1996_06
- Patentnummer
- US05523424
Notizen zur Reaktion
Wird geladen…