Premium
The Use of Trifluoroacetyl as an N‐ and O‐Protecting Group during the Synthesis of Energetic Compounds containing Nitramine and/or Nitrate Ester Groups
Author(s) -
Bellamy Anthony J.,
MacCuish Alistair,
Golding Peter,
Mahon Mary F.
Publication year - 2007
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.200700004
Subject(s) - nitration , chemistry , solvolysis , amine gas treating , hydroxymethyl , protecting group , nitrate , organic chemistry , group (periodic table) , medicinal chemistry , hydrolysis , alkyl
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.