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The Use of theTrifluoroacetyl Protecting Group in the Synthesis of Mono‐ (4) and Di‐Amines (4,10) in the Polynitrohexaazaisowurtzitane Series
Author(s) -
Bellamy Anthony J.,
MacCuish Alistair,
Golding Peter
Publication year - 2003
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.200390023
Subject(s) - amine gas treating , group (periodic table) , selectivity , protecting group , chemistry , organic chemistry , catalysis , alkyl
The first rational synthesis of the mono‐amine 2,6,8,10,12‐pentanitro‐2,4,6,8,10,12‐hexaazaisowurtzitane (II) and the di‐amine 2,6,8,12‐tetranitro‐2,4,6,8,10,12‐hexaazaisowurtzitane (III) is described. Both syntheses exploit the selectivity, under nitrolysis conditions, between an N‐acetyl group and an N‐trifluoroacetyl group, and the ease with which an N‐trifluoroacetyl group can be hydrolytically removed.