Edwin M. Smolin, Central Research Division, American Cyanamid Company, Stamford, Connecticut.Lorence Rapoport, Central Research Division, American Cyanamid Company, Stamford, Connecticut.

• Introduction 1I. Cyanuric Acid and Derivatives 17I. Introduction 17II. Cyanunc Acid 20III. Cyanuric Halides 48IV. Cyanuric Acid Esters 67V. Acyloxy-s-triazines 90VI. Cyanuric Azides 100VII. Thiocyanuric Acids 105VIII. Triazinylthioglycolic Acids and Their Derivatives 114IX. 2.4.6-Tri(acetonylthio).s.triazine 115X. Triselenocyanuric Acid 116XI. Esters of s-Triazine-2,4.6-triphosphonite 117XII. Uses and Industrial Applications of Cyanuric Chloride and Derivatives 117II. Alkyl(Ary1)-s-triazines 147I. Introduction 147II. General Synthetic Methods 149III. Reactions 162IV. Trialkyl-s-Triazines 165V. Triaryl-s-triazines 171VI. Alkyl-aryl-s-Triazines 179VII. Alkyl-aryl-dihydro-s-triazines 179VIII. Applications 182III. Monohydroxy-, Hydroxyamino-, Dihydroxy-s-triazines and Related Compounds 185I. Monohydroxy-s-triazines 185II. Monochloro-s-triazines 185III. Hydroxyamino-s-triazines 187IV. Dihydroxy-s-triazines 202V. Hydrogenated Derivatives 209VI. Dihalo-s-triazines 214lV. Monoamino- and Diamino-s-triazines 217I. Monoamino-s-triazines 217II. Diamino-s-triazines 222III. Diamino dihydro-s-triazines 258V. Ammelide. Ammeline. and Related Compounds 269I. Ammelide 269II. Ammelide Ethers 274III. Aminodichloro-s-triazines 279IV.Ammeline 281V. Ammeline Ethers 285VI. Diaminochloro-s-triazines 292VII. Dithioammelide 297VIII. Thioammeline 298IX. Thioammeline Ethers 301X. Related Compounds 305VI. Melamine and Substituted Melamines 309I. Introduction 309II. Physical Properties 309III. Synthesis of Melamine 309IV. Reactions of Melamine 321V. Structure 348VI. Substituted "Normal" Melamines 349VII. Applications of Melamine and Derivatives 373VIII. IsomelaminES 379VII. Isocyanuric Acid and Derivatives 389I. Isocyanuric Acid 389II. 1.3.5.Trihalo.2.4.6.trioxohexahydro-s-triazines 390III. Esters ofIsocyanuric Acid 393IV. Isothiocyanuric Acid 416V. Other Isocyanuric Compounds 420VIII. Condensed Ring s-Triazine Systems 423I.Endo Compounds 423II. Condensed Five-Membered Ring Compounds 426III. Condensed-Six-Membered Ring Compounds 445IX. Hexahydro-s-triazines 473I. Introduction 473II. Hexahydro-s-triazine and Nitrate 473III. 1.3.5.Trialkylhexahydro-s-triazine 476IV. Aryl and Arylalkylhexahydro-s-triazines 490V. 2.4,6-Trialkyl- and Triarylhexahydro-s-triazines 505VI. Halogen Derivatives of Hexahydro-s-triazine and Alkylhexahydro-s-triazines 506VII. Nitro- and Nitrosohexahydro-s-triazines 509VIII. Amino Derivatives of Hexahydro-s-triazines 526IX. Sulfonyl Derivatives 528X. Hydroxy Derivatives: 1.3.5-Trihydroxyhexahydro-s-triazines 1,3,5-Trinitrosohexahydros-s-triazines 531XI. Carbonyl (Acyl) Derivatives 533XII. Oxo and Thion Derivatives 536XIII. Carboxylic Acid Derivatives 539XIV. 1-Sulfo-4-alkylhexahydro.2,4,6-triazines 540X. Hexamethylenetetramine 545I. Introduction 545II. Structure 545III. Formation 546IV. Physical Properties 550V. Preparation 551VI. Reactions 552VII. Detection and Analysis of Hexamethylenetetramie 588VIII. Uses of Hexamethylenetetramine 588XI. s-Triazaborane and Its Derivatives 597I. Introduction 597II. s-Triazaborane 597III. Alkyl Derivatives of s-Triazaborane 607IV. Halogen Derivatives of s-Triazaborane 619V. Hydroxy-s-triazaboranes 624VI. Methoxy-s-triazaboranes 624VII. Other s-Triazaborane Derivatives 625

Edwin M. Smolin, Central Research Division, American Cyanamid Company, Stamford, Connecticut.Lorence Rapoport, Central Research Division, American Cyanamid Company, Stamford, Connecticut.

• Introduction 1I. Cyanuric Acid and Derivatives 17I. Introduction 17II. Cyanunc Acid 20III. Cyanuric Halides 48IV. Cyanuric Acid Esters 67V. Acyloxy-s-triazines 90VI. Cyanuric Azides 100VII. Thiocyanuric Acids 105VIII. Triazinylthioglycolic Acids and Their Derivatives 114IX. 2.4.6-Tri(acetonylthio).s.triazine 115X. Triselenocyanuric Acid 116XI. Esters of s-Triazine-2,4.6-triphosphonite 117XII. Uses and Industrial Applications of Cyanuric Chloride and Derivatives 117II. Alkyl(Ary1)-s-triazines 147I. Introduction 147II. General Synthetic Methods 149III. Reactions 162IV. Trialkyl-s-Triazines 165V. Triaryl-s-triazines 171VI. Alkyl-aryl-s-Triazines 179VII. Alkyl-aryl-dihydro-s-triazines 179VIII. Applications 182III. Monohydroxy-, Hydroxyamino-, Dihydroxy-s-triazines and Related Compounds 185I. Monohydroxy-s-triazines 185II. Monochloro-s-triazines 185III. Hydroxyamino-s-triazines 187IV. Dihydroxy-s-triazines 202V. Hydrogenated Derivatives 209VI. Dihalo-s-triazines 214lV. Monoamino- and Diamino-s-triazines 217I. Monoamino-s-triazines 217II. Diamino-s-triazines 222III. Diamino dihydro-s-triazines 258V. Ammelide. Ammeline. and Related Compounds 269I. Ammelide 269II. Ammelide Ethers 274III. Aminodichloro-s-triazines 279IV.Ammeline 281V. Ammeline Ethers 285VI. Diaminochloro-s-triazines 292VII. Dithioammelide 297VIII. Thioammeline 298IX. Thioammeline Ethers 301X. Related Compounds 305VI. Melamine and Substituted Melamines 309I. Introduction 309II. Physical Properties 309III. Synthesis of Melamine 309IV. Reactions of Melamine 321V. Structure 348VI. Substituted "Normal" Melamines 349VII. Applications of Melamine and Derivatives 373VIII. IsomelaminES 379VII. Isocyanuric Acid and Derivatives 389I. Isocyanuric Acid 389II. 1.3.5.Trihalo.2.4.6.trioxohexahydro-s-triazines 390III. Esters ofIsocyanuric Acid 393IV. Isothiocyanuric Acid 416V. Other Isocyanuric Compounds 420VIII. Condensed Ring s-Triazine Systems 423I.Endo Compounds 423II. Condensed Five-Membered Ring Compounds 426III. Condensed-Six-Membered Ring Compounds 445IX. Hexahydro-s-triazines 473I. Introduction 473II. Hexahydro-s-triazine and Nitrate 473III. 1.3.5.Trialkylhexahydro-s-triazine 476IV. Aryl and Arylalkylhexahydro-s-triazines 490V. 2.4,6-Trialkyl- and Triarylhexahydro-s-triazines 505VI. Halogen Derivatives of Hexahydro-s-triazine and Alkylhexahydro-s-triazines 506VII. Nitro- and Nitrosohexahydro-s-triazines 509VIII. Amino Derivatives of Hexahydro-s-triazines 526IX. Sulfonyl Derivatives 528X. Hydroxy Derivatives: 1.3.5-Trihydroxyhexahydro-s-triazines 1,3,5-Trinitrosohexahydros-s-triazines 531XI. Carbonyl (Acyl) Derivatives 533XII. Oxo and Thion Derivatives 536XIII. Carboxylic Acid Derivatives 539XIV. 1-Sulfo-4-alkylhexahydro.2,4,6-triazines 540X. Hexamethylenetetramine 545I. Introduction 545II. Structure 545III. Formation 546IV. Physical Properties 550V. Preparation 551VI. Reactions 552VII. Detection and Analysis of Hexamethylenetetramie 588VIII. Uses of Hexamethylenetetramine 588XI. s-Triazaborane and Its Derivatives 597I. Introduction 597II. s-Triazaborane 597III. Alkyl Derivatives of s-Triazaborane 607IV. Halogen Derivatives of s-Triazaborane 619V. Hydroxy-s-triazaboranes 624VI. Methoxy-s-triazaboranes 624VII. Other s-Triazaborane Derivatives 625