The Use of Trifluoroacetyl as an N‐ and O‐Protecting Group during the Synthesis of Energetic Compounds containing Nitramine and/or Nitrate Ester Groups

Abstract

Abstract N‐ and O‐Trifluoroacetylation has been used to protect secondary amine groups and hydroxyl groups respectively under nitrolysis/nitration conditions. The trifluoroacetyl protecting group may be readily removed from the nitrated products by solvolysis under mild conditions. The energetic molecules that have been produced by this methodology include 2,6,8,12‐tetranitro‐ and 2,4,6,8,12‐pentanitro‐2,4,6,8,10,12‐hexaazaisowurtzitane, 2‐hydroxymethyl‐2‐methyl‐1,3‐dinitratopropane [2,2‐bis(nitratomethyl)‐propan‐1‐ol] and N‐nitroazetidin‐3‐ol.