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Foreword | |
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Preface | |
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Abbreviations | |
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Acknowledgements | |
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Background | |
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Synthetic Routes to Aliphatic C-Nitro Functionality | |
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Introduction | |
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Aliphatic C-nitro compounds as explosives | |
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Direct nitration of alkanes | |
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Addition of nitric acid, nitrogen oxides and related compounds to unsaturated bonds | |
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Nitric acid and its mixtures | |
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Nitrogen dioxide | |
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Dinitrogen pentoxide | |
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Nitrous oxide and dinitrogen trioxide | |
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Other nitrating agents | |
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Halide displacement | |
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Victor Meyer reaction | |
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Modified Victor Meyer reaction | |
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Ter Meer reaction | |
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Displacements using nitronate salts as nucleophiles | |
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Oxidation and nitration of C-N bonds | |
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Oxidation and nitration of oximes | |
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Oxidation of amines | |
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Nitration of nitronate salts | |
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Oxidation of pseudonitroles | |
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Oxidation of isocyanates | |
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Oxidation of nitrosoalkanes | |
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Kaplan-Shechter reaction | |
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Nitration of compounds containing acidic hydrogen | |
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Alkaline nitration | |
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Acidic nitration | |
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Oxidative dimerization | |
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Addition and condensation reactions | |
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1,2-Addition reactions | |
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1,4-Addition reactions | |
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Mannich reaction | |
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Henry reaction | |
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Derivatives of polynitroaliphatic alcohols | |
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Miscellaneous | |
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1,1-Diamino-2,2-dinitroethylenes | |
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Other routes to aliphatic nitro compounds | |
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Selective reductions | |
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Chemical stability of polynitroaliphatic compounds | |
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Reactions with mineral acids | |
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Reactions with base and nucleophiles | |
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References | |
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Energetic Compounds 1: Polynitropolycycloalkanes | |
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Caged structures as energetic materials | |
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Cyclopropanes and spirocyclopropanes | |
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Cyclobutanes and their derivatives | |
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Cubanes | |
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Homocubanes | |
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Prismanes | |
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Adamantanes | |
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Polynitrobicycloalkanes | |
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Norbomanes | |
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Bicyclo[3.3.0]octane | |
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Bicyclo[3.3,1]nonane | |
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References | |
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Synthetic Routes to Nitrate Esters | |
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Nitrate esters as explosives | |
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Nitration of the parent alcohol | |
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O-Nitration with nitric acid and its mixtures | |
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O-Nitration with dinitrogen tetroxide | |
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O-Nitration with dinitrogen pentoxide | |
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O-Nitration with nitronium salts | |
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Transfer nitration | |
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Other O-nitrating agents | |
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Nucleophilic displacement with nitrate anion | |
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Metathesis between alkyl halides and silver nitrate | |
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Decomposition of nitratocarbonates | |
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Displacement of sulfonate esters with nitrate anion | |
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Displacement with mercury (I) nitrate | |
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Nitrate esters from the ring-opening of strained oxygen heterocycles | |
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Ring-opening nitration of epoxides | |
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1,3-Dinitrate esters from the ring-opening nitration of oxetanes with dinitrogen pentoxide | |
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Other oxygen heterocycles | |
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Nitrodesilylation | |
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Additions to alkenes | |
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Nitric acid and its mixtures | |
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Nitrogen oxides | |
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Metal salts | |
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Halonitroxylation | |
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Deamination | |
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Miscellaneous methods | |
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Synthetic routes to some polyols and their nitrate ester derivatives | |
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Energetic nitrate esters | |
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References | |
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Synthetic Routes to Aromatic C-Nitro Compounds | |
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Introduction | |
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Polynitroarylenes as explosives | |
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Nitration | |
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Nitration with mixed acid | |
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Substrate derived reactivity | |
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Effect of nitrating agent and reaction conditions on product selectivity | |
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Other nitrating agents | |
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Side-reactions and by-products from nitration | |
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Nitrosation-oxidation | |
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Nitramine rearrangement | |
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Reaction of diazonium salts with nitrite anion | |
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Oxidation of arylamines, arylhydroxylamines and other derivatives | |
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Oxidation of arylamines and their derivatives | |
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Oxidation of arylhydroxylamines and their derivatives | |
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Nucleophilic aromatic substitution | |
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Displacement of halide | |
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Nitro group displacement and the reactivity of polynitroarylenes | |
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Displacement of other groups | |
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Synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) | |
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The chemistry of 2,4,6-trinitrotoluene (TNT) | |
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Conjugation and thermally insensitive explosives | |
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References | |
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Synthetic Routes to N-Nitro Functionality | |
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Introduction | |
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Nitramines, nitramides and nitrimines as explosives | |
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Direct nitration of amines | |
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Nitration under acidic conditions | |
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Nitration with nonacidic reagents | |
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Nitration of chloramines | |
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Nitration of dialkylchloramines | |
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Nitration of alkyldichloramines | |
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N-Nitration of amides and related compounds | |
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Nitration with acidic reagents | |
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Nitration with nonacidic reagents | |
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Nitrolysis | |
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Nitrolysis of amides and their derivatives | |
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Nitrolysis of N-alkyl bonds | |
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Nitrolysis of nitrosamines | |
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Nitrative cleavage of other nitrogen bonds | |
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Ring-opening nitration of strained nitrogen heterocycles | |
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Aziridines | |
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Azetidines | |
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Nitrosamine oxidation | |
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Hydrolysis of nitramides and nitroureas | |
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Dehydration of nitrate salts | |
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Other methods | |
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Primary nitramines as nucleophiles | |
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1,4-Michael addition reactions | |
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Mannich condensation reactions | |
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Condensations with formaldehyde | |
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Nucleophilic displacement reactions | |
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Aromatic nitramines | |
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The nitrolysis of hexamine | |
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The synthesis of RDX | |
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The synthesis of HMX | |
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Effect of reaction conditions on the nitrolysis of hexamine | |
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Other nitramine products from the nitrolysis of hexamine | |
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References | |
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Energetic Compounds 2: Nitramines and Their Derivatives | |
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Cyclopropanes | |
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Cyclobutanes | |
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Azetidines - 1,3,3-trinitroazetidine (TNAZ) | |
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Cubane-based nitramines | |
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Diazocines | |
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Bicycles | |
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Caged heterocycles - isowurtzitanes | |
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Heterocyclic nitramines derived from Mannich reactions | |
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Nitroureas | |
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Other energetic nitramines | |
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Energetic groups | |
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Dinitramide anion | |
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Alkyl N,N-dinitramines | |
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N-Nitroimides | |
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References | |
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Energetic Compounds 3: N-Heterocycles | |
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Introduction | |
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5-Membered rings - 1N - pyrroles | |
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5-Membered rings - 2N | |
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Pyrazoles | |
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Imidazoles | |
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1,3,4-Oxadiazoles | |
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1,2,5-Oxadiazoles (furazans) | |
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Benzofurazans | |
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Furoxans | |
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Benzofuroxans | |
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5-Membered rings - 3N | |
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Triazoles | |
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Triazolones | |
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Benzotriazoles | |
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5-Membered rings - 4N | |
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6-Membered rings - 1N - pyridines | |
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6-Membered rings - 2N | |
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6-Membered rings - 3N | |
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6-Membered rings - 4N | |
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Dibenzotetraazapentalenes | |
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References | |
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Miscellaneous Explosive Compounds | |
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Organic azides | |
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Alkyl azides | |
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Aromatic azides | |
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Peroxides | |
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Diazophenols | |
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Diazophenols from the diazotization of aminophenols | |
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Diazophenols from the rearrangement of o-nitroarylnitramines | |
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Nitrogen-rich compounds from guanidine and its derivatives | |
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References | |
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Dinitrogen Pentoxide - An Eco-Friendly Nitrating Agent | |
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Introduction | |
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Nitrations with dinitrogen pentoxide | |
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The chemistry of dinitrogen pentoxide | |
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Preparation of dinitrogen pentoxide | |
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C-nitration | |
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W-nitration | |
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Nitrolysis | |
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O-nitration | |
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Ring cleavage nitration | |
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Selective O-nitration | |
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Glycidyl nitrate and NIMMO - batch reactor verses flow reactor | |
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Synthesis of the high performance and eco-friendly oxidizer - ammonium dinitramide | |
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References | |
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Index | |