- Reactions of 2-Fluoro-2-nitro-1,3-propanediol. Trifluoromethanesulfonates and 3-Fluoro-3-nitrooxetane
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The reaction of diethyl fluoronitromalonate with base and formaldehyde provided a convenient synthesis of 2-fluoro-2-nitro-1,3-propanediol.This diol reacted with triflic anhydride to give 2-fluoro-3-hydroxy-2-nitro-1-propyl triflate and 2-fluoro-2-nitro-1,3-propylene ditriflate.The monotriflate reacted with base to give 3-fluoro-3-nitrooxetane.The ditriflate underwent displacement reactions with sodium azide, 2-fluoro-2,2-dinitroethanol, and methanol.Reactions of 3-fluoro-3-nitrooxetane with strong acids resulted in ring opening to give 3-substituted 2-fluoro-2-nitropropanols.The oxetane was polymerized with phosphorus pentafluoride.Triflates derived from 2,2-dinitro-1,3-propanediol and 2-(hydroxymethyl)-2-nitro-1,3-propanediol did not cyclize.
- Berkowitz, Phillip T.,Baum, Kurt
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- 3-Fluoro-3-nitrooxetane
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3-Fluoro-3-nitrooxetane is prepared by a method which comprises reacting luoro-2-nitro propanediol with trifluoro methane sulfonic anhydride, separating the reaction product and then further reacting the reaction product with a base. The oxetane may be polymerized to form a nitro containing polyether which is useful as a binder material for explosives or propellants.
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