The Journal of Organic Chemistry

Reactions of 2-fluoro-2-nitro-1, 3-propanediol. Trifluoromethanesulfonates and 3-fluoro-3-nitrooxetane

PT Berkowitz, K Baum

Index: Berkowitz, Phillip T.; Baum, Kurt Journal of Organic Chemistry, 1980 , vol. 45, # 24 p. 4853 - 4857

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Citation Number: 17

Abstract

The reaction of diethyl fluoronitromalonate with base and formaldehyde provided a convenient synthesis of 2-fluoro-2-nitro-l, 3-propanediol. This diol reacted with triflic anhydride to give 2-fluorc-3-hydroxy-2-nitro-l-propyl triflate and 2-fluoro-2-nitro-l, 3- propylene ditriflate. The monotriflate reacted with base to give 3-fluoro-3-nitrooxetme. The ditriflate underwent displacement reactions with sodium azide, 2-fluoro-2, 2-dinitroethanol, ...