Detailed table of contents (pdf)

XXXVIII Table of Contents
17.2.3.5.1.1.1 Fragments P—C, P—C, and P—C ............................................ 567
17.2.3.5.1.1.1.1 Method 1: Transition-Metal-Catalyzed Cyclotrimerization of
Phosphaalkynes ........................................... 567
17.2.3.5.2 Aromatization ............................................................ 570
17.2.3.5.2.1 Method 1: Dehalogenation of 1,3,5-Trichloro-1,3,5-triphosphinanes .... 570
17.3 Product Class 3: Six-Membered Hetarenes with More Than
Three Heteroatoms
M. Bohle
17.3 Product Class 3: Six-Membered Hetarenes with More
Than Three Heteroatoms ................................................ 585
17.3.1 Product Subclass 1: 1,2,3,4-Tetrazines ................................... 585
17.3.1.1 Method 1: Synthesis of 1,2,3,4-Tetrazine N-Oxides .................... 586
17.3.1.1.1 Variation 1: Via Diazotization .......................................... 586
17.3.1.1.2 Variation 2: Via Nitration .............................................. 588
17.3.2 Product Subclass 2: 1,2,3,5-Tetrazines ................................... 588
17.3.3 Product Subclass 3: 1,2,4,5-Tetrazines ................................... 589
17.3.3.1 Synthesis by Ring-Closure Reactions ....................................... 592
17.3.3.1.1 By Formation of Four N—C Bonds .......................................... 593
17.3.3.1.1.1 Fragments N—N, N—N, and Two C Fragments .............................. 593
17.3.3.1.1.1.1 Method 1: Dimerization of Activated Hydrazidic Acid Derivatives ....... 593
17.3.3.1.1.1.1.1 Variation 1: From Nitriles .............................................. 593
17.3.3.1.1.1.1.2 Variation 2: From Carboxylic Acid Derivatives ........................... 594
17.3.3.1.1.1.1.3 Variation 3: From Carbonyl Compounds ................................ 596
17.3.3.1.1.1.1.4 Variation 4: From Alkenes (Masked Carbonyl Compounds) .............. 597
17.3.3.1.2 By Formation of Two N—C Bonds .......................................... 598
17.3.3.1.2.1 Fragments C—N—N—C and N—N ........................................... 598
17.3.3.1.2.1.1 Method 1: Oxidation of Dihydrotetrazines ............................ 598
17.3.3.1.2.2 Fragments N—N—C and N—N—C ........................................... 600
17.3.3.1.2.2.1 Method 1: Dimerization of Diazo Compounds ......................... 600
17.3.3.1.2.2.2 Method 2: Dimerization of Nitrile Imines .............................. 602
17.3.3.1.2.3 Fragments N—N—C—N—N and C ........................................... 602
17.3.3.1.2.3.1 Method 1: From Hydrazonohydrazides ................................ 602
17.3.3.1.2.3.2 Method 2: From Guanidine-1,2,3-triamine ............................ 603
17.3.3.1.2.3.3 Method 3: From Carbohydrazides .................................... 604
17.3.3.1.2.3.4 Method 4: From Thiocarbohydrazides and Related Compounds ........ 605
17.3.3.1.3 By Formation of One N—C Bond ........................................... 606
17.3.3.1.3.1 Fragment C—N—N—C—N—N ............................................... 606
17.3.3.1.3.1.1 Method 1: By Cyclization of Tetrazolylguanidines ...................... 606