The use of trifluoroacetyl as an N- and O-protecting group during the synthesis of energetic compounds containing nitramine and/or nitrate ester groups

A J Bellamy, A MacCuish, P Golding, M F Mahon

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10 Citations (Scopus)

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-metbyl-1,3-dinitratopropane [2,2-bis(nitratomethyl)-propan-l-ol] and N-nitroazetidin-3-ol.
Original languageEnglish
Pages (from-to)20-31
Number of pages12
JournalPropellants, Explosives, Pyrotechnics
Volume32
Issue number1
DOIs
Publication statusPublished - 2007

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Nitration
Hydroxyl Radical
Nitrates
Amines
Esters
Molecules
nitramine

Cite this

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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-metbyl-1,3-dinitratopropane [2,2-bis(nitratomethyl)-propan-l-ol] and N-nitroazetidin-3-ol.",
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T1 - The use of trifluoroacetyl as an N- and O-protecting group during the synthesis of energetic compounds containing nitramine and/or nitrate ester groups

AU - Bellamy, A J

AU - MacCuish, A

AU - Golding, P

AU - Mahon, M F

N1 - ID number: ISI:000244508900004

PY - 2007

Y1 - 2007

N2 - 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-metbyl-1,3-dinitratopropane [2,2-bis(nitratomethyl)-propan-l-ol] and N-nitroazetidin-3-ol.

AB - 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-metbyl-1,3-dinitratopropane [2,2-bis(nitratomethyl)-propan-l-ol] and N-nitroazetidin-3-ol.

U2 - 10.1002/prep.200700004

DO - 10.1002/prep.200700004

M3 - Article

VL - 32

SP - 20

EP - 31

JO - Propellants, Explosives, Pyrotechnics

JF - Propellants, Explosives, Pyrotechnics

SN - 0721-3115

IS - 1

ER -