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s-Triazines and Derivatives, Volume 13



s-Triazines and Derivatives, Volume 13

Edwin M. Smolin (Editor), Lorence Rapoport (Editor)

ISBN: 978-0-470-18812-5 September 2009 668 Pages

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The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects – properties, synthesis, reactions, physiological and industrial significance – of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

Introduction 1

I. Cyanuric Acid and Derivatives 17

I. Introduction 17

II. Cyanunc Acid 20

III. Cyanuric Halides 48

IV. Cyanuric Acid Esters 67

V. Acyloxy-s-triazines 90

VI. Cyanuric Azides 100

VII. Thiocyanuric Acids 105

VIII. Triazinylthioglycolic Acids and Their Derivatives 114

IX. 2.4.6-Tri(acetonylthio).s.triazine 115

X. Triselenocyanuric Acid 116

XI. Esters of s-Triazine-2,4.6-triphosphonite 117

XII. Uses and Industrial Applications of Cyanuric Chloride and Derivatives 117

II. Alkyl(Ary1)-s-triazines 147

I. Introduction 147

II. General Synthetic Methods 149

III. Reactions 162

IV. Trialkyl-s-Triazines 165

V. Triaryl-s-triazines 171

VI. Alkyl-aryl-s-Triazines 179

VII. Alkyl-aryl-dihydro-s-triazines 179

VIII. Applications 182

III. Monohydroxy-, Hydroxyamino-, Dihydroxy-s-triazines and Related Compounds 185

I. Monohydroxy-s-triazines 185

II. Monochloro-s-triazines 185

III. Hydroxyamino-s-triazines 187

IV. Dihydroxy-s-triazines 202

V. Hydrogenated Derivatives 209

VI. Dihalo-s-triazines 214

lV. Monoamino- and Diamino-s-triazines 217

I. Monoamino-s-triazines 217

II. Diamino-s-triazines 222

III. Diamino dihydro-s-triazines 258

V. Ammelide. Ammeline. and Related Compounds 269

I. Ammelide 269

II. Ammelide Ethers 274

III. Aminodichloro-s-triazines 279

IV.Ammeline 281

V. Ammeline Ethers 285

VI. Diaminochloro-s-triazines 292

VII. Dithioammelide 297

VIII. Thioammeline 298

IX. Thioammeline Ethers 301

X. Related Compounds 305

VI. Melamine and Substituted Melamines 309

I. Introduction 309

II. Physical Properties 309

III. Synthesis of Melamine 309

IV. Reactions of Melamine 321

V. Structure 348

VI. Substituted "Normal" Melamines 349

VII. Applications of Melamine and Derivatives 373

VIII. IsomelaminES 379

VII. Isocyanuric Acid and Derivatives 389

I. Isocyanuric Acid 389

II. 1.3.5.Trihalo.2.4.6.trioxohexahydro-s-triazines 390

III. Esters ofIsocyanuric Acid 393

IV. Isothiocyanuric Acid 416

V. Other Isocyanuric Compounds 420

VIII. Condensed Ring s-Triazine Systems 423

I.Endo Compounds 423

II. Condensed Five-Membered Ring Compounds 426

III. Condensed-Six-Membered Ring Compounds 445

IX. Hexahydro-s-triazines 473

I. Introduction 473

II. Hexahydro-s-triazine and Nitrate 473

III. 1.3.5.Trialkylhexahydro-s-triazine 476

IV. Aryl and Arylalkylhexahydro-s-triazines 490

V. 2.4,6-Trialkyl- and Triarylhexahydro-s-triazines 505

VI. Halogen Derivatives of Hexahydro-s-triazine and Alkylhexahydro-s-triazines 506

VII. Nitro- and Nitrosohexahydro-s-triazines 509

VIII. Amino Derivatives of Hexahydro-s-triazines 526

IX. Sulfonyl Derivatives 528

X. Hydroxy Derivatives: 1.3.5-Trihydroxyhexahydro-s-triazines 1,3,5-Trinitrosohexahydros-s-triazines 531

XI. Carbonyl (Acyl) Derivatives 533

XII. Oxo and Thion Derivatives 536

XIII. Carboxylic Acid Derivatives 539

XIV. 1-Sulfo-4-alkylhexahydro.2,4,6-triazines 540

X. Hexamethylenetetramine 545

I. Introduction 545

II. Structure 545

III. Formation 546

IV. Physical Properties 550

V. Preparation 551

VI. Reactions 552

VII. Detection and Analysis of Hexamethylenetetramie 588

VIII. Uses of Hexamethylenetetramine 588

XI. s-Triazaborane and Its Derivatives 597

I. Introduction 597

II. s-Triazaborane 597

III. Alkyl Derivatives of s-Triazaborane 607

IV. Halogen Derivatives of s-Triazaborane 619

V. Hydroxy-s-triazaboranes 624

VI. Methoxy-s-triazaboranes 624

VII. Other s-Triazaborane Derivatives 625