Detailed table of contents (pdf)
Detailed table of contents (pdf) 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
Table of Contents XXXIX 17.3.3.2 Synthesis by Ring Transformation .......................................... 607 17.3.3.3 Aromatization .......................................................... 608 17.3.3.4 Synthesis by Substituent Modification ..................................... 608 17.3.3.4.1 Substitution of Existing Substituents ....................................... 608 17.3.3.4.1.1 Of Hydrogen .......................................................... 608 17.3.3.4.1.2 Of Carbon Functionalities ................................................. 609 17.3.3.4.1.3 Of Heteroatoms .......................................................... 610 17.3.3.4.1.3.1 Method 1: Substitution of Halogen Substituents ...................... 610 17.3.3.4.1.3.2 Method 2: Substitution of Oxygen Substituents ....................... 612 17.3.3.4.1.3.3 Method 3: Substitution of Sulfur Substituents ......................... 613 17.3.3.4.1.3.4 Method 4: Substitution of Nitrogen Substituents ...................... 614 17.3.3.4.2 Addition of Heteroatoms (N-Oxidation) .................................... 615 17.3.3.4.3 Modification of Substituents .............................................. 616 17.4 Product Class 4: Seven-Membered Hetarenes with One Heteroatom 17.4.1 Product Subclass 1: Oxepins S. von Angerer 17.4.1 Product Subclass 1: Oxepins ............................................. 627 17.4.1.1 Synthesis by Ring-Closure Reactions ....................................... 630 17.4.1.1.1 By Formation of One O—C and One C—C Bond ............................. 630 17.4.1.1.1.1 Method 1: From Cyclopropenes and Alk-1-ynes ....................... 630 17.4.1.1.2 By Formation of One O—C Bond ........................................... 631 17.4.1.1.2.1 Method 1: Synthesis from Acyclic Precursors .......................... 631 17.4.1.2 Synthesis by Ring Transformation .......................................... 631 17.4.1.2.1 Method 1: Valence Isomerization of 3-Oxatricycloheptenes ............ 631 17.4.1.2.2 Method 2: Valence Isomerization of 3-Oxaquadricyclanes .............. 632 17.4.1.2.3 Method 3: Valence Isomerization of 7-Oxanorbornadienes ............. 636 17.4.1.2.4 Method 4: Ring Enlargement of Cyclohexa-1,4-dienes ................. 638 17.4.1.2.5 Method 5: Ring Enlargement of 4H-Pyrans ............................ 639 17.4.1.3 Aromatization ............................................................ 640 17.4.1.3.1 Method 1: By Dehydrohalogenation .................................. 640 17.4.1.3.2 Method 2: By Dehalogenation ........................................ 646 17.4.1.3.3 Method 3: By Decarboxylation ....................................... 647 17.4.1.4 Synthesis by Substituent Modification ..................................... 648 17.4.1.4.1 Substitution of Existing Substituents ....................................... 648 17.4.1.4.1.1 Of Hydrogen .............................................................. 648 17.4.1.4.1.2 Of Bromine ............................................................... 648
- Page 1 and 2: Table of Contents IX Volume 17: Six
- Page 3 and 4: Table of Contents XI Table of Conte
- Page 5 and 6: Table of Contents XIII 17.1.1.2.4.1
- Page 7 and 8: Table of Contents XV 17.1.2.3.1.3 B
- Page 9 and 10: Table of Contents XVII 17.1.3.2 1,4
- Page 11 and 12: Table of Contents XIX 17.1.3.3.1.1.
- Page 13 and 14: Table of Contents XXI 17.2 Product
- Page 15 and 16: Table of Contents XXIII 17.2.1.2.1.
- Page 17 and 18: Table of Contents XXV 17.2.1.3.1.1
- Page 19 and 20: Table of Contents XXVII 17.2.2 Prod
- Page 21 and 22: Table of Contents XXIX 17.2.2.1.3.3
- Page 23 and 24: Table of Contents XXXI 17.2.2.2.1.4
- Page 25 and 26: Table of Contents XXXIII 17.2.3.1.1
- Page 27 and 28: Table of Contents XXXV 17.2.3.1.2.2
- Page 29: Table of Contents XXXVII 17.2.3.1.4
- Page 33 and 34: Table of Contents XLI 17.4.2.2.2.2
- Page 35 and 36: Table of Contents XLIII 17.4.4.1.2.
- Page 37 and 38: Table of Contents XLV 17.4.5.1.2.3
- Page 39 and 40: Table of Contents XLVII 17.4.5.4.1.
- Page 41 and 42: Table of Contents XLIX 17.4.6.2.4.2
- Page 43 and 44: Table of Contents LI 17.4.6.5.4.2 A
- Page 45 and 46: Table of Contents LIII 17.4.6.7.4.4
- Page 47 and 48: Table of Contents LV 17.5.2.2.1 Met
- Page 49 and 50: Table of Contents LVII 17.6.2.1.1.4
- Page 51 and 52: Table of Contents LIX 17.6.5.2.2.1.
- Page 53 and 54: Table of Contents LXI 17.7.3.2 [2.3
- Page 55 and 56: Table of Contents LXIII 17.7.5.1.2.
- Page 57 and 58: Table of Contents LXV 17.8.3.2 Cont
- Page 59 and 60: Table of Contents LXVII 17.9.8.3 Me
- Page 61: Table of Contents LXIX 17.9.22.3 Me
Table <strong>of</strong> Contents XXXIX<br />
17.3.3.2 Synthesis by Ring Transformation .......................................... 607<br />
17.3.3.3 Aromatization .......................................................... 608<br />
17.3.3.4 Synthesis by Substituent Modification ..................................... 608<br />
17.3.3.4.1 Substitution <strong>of</strong> Existing Substituents ....................................... 608<br />
17.3.3.4.1.1 Of Hydrogen .......................................................... 608<br />
17.3.3.4.1.2 Of Carbon Functionalities ................................................. 609<br />
17.3.3.4.1.3 Of Heteroatoms .......................................................... 610<br />
17.3.3.4.1.3.1 Method 1: Substitution <strong>of</strong> Halogen Substituents ...................... 610<br />
17.3.3.4.1.3.2 Method 2: Substitution <strong>of</strong> Oxygen Substituents ....................... 612<br />
17.3.3.4.1.3.3 Method 3: Substitution <strong>of</strong> Sulfur Substituents ......................... 613<br />
17.3.3.4.1.3.4 Method 4: Substitution <strong>of</strong> Nitrogen Substituents ...................... 614<br />
17.3.3.4.2 Addition <strong>of</strong> Heteroatoms (N-Oxidation) .................................... 615<br />
17.3.3.4.3 Modification <strong>of</strong> Substituents .............................................. 616<br />
17.4 Product Class 4: Seven-Membered Hetarenes with One Heteroatom<br />
17.4.1 Product Subclass 1: Oxepins<br />
S. von Angerer<br />
17.4.1 Product Subclass 1: Oxepins ............................................. 627<br />
17.4.1.1 Synthesis by Ring-Closure Reactions ....................................... 630<br />
17.4.1.1.1 By Formation <strong>of</strong> One O—C and One C—C Bond ............................. 630<br />
17.4.1.1.1.1 Method 1: From Cyclopropenes and Alk-1-ynes ....................... 630<br />
17.4.1.1.2 By Formation <strong>of</strong> One O—C Bond ........................................... 631<br />
17.4.1.1.2.1 Method 1: Synthesis from Acyclic Precursors .......................... 631<br />
17.4.1.2 Synthesis by Ring Transformation .......................................... 631<br />
17.4.1.2.1 Method 1: Valence Isomerization <strong>of</strong> 3-Oxatricycloheptenes ............ 631<br />
17.4.1.2.2 Method 2: Valence Isomerization <strong>of</strong> 3-Oxaquadricyclanes .............. 632<br />
17.4.1.2.3 Method 3: Valence Isomerization <strong>of</strong> 7-Oxanorbornadienes ............. 636<br />
17.4.1.2.4 Method 4: Ring Enlargement <strong>of</strong> Cyclohexa-1,4-dienes ................. 638<br />
17.4.1.2.5 Method 5: Ring Enlargement <strong>of</strong> 4H-Pyrans ............................ 639<br />
17.4.1.3 Aromatization ............................................................ 640<br />
17.4.1.3.1 Method 1: By Dehydrohalogenation .................................. 640<br />
17.4.1.3.2 Method 2: By Dehalogenation ........................................ 646<br />
17.4.1.3.3 Method 3: By Decarboxylation ....................................... 647<br />
17.4.1.4 Synthesis by Substituent Modification ..................................... 648<br />
17.4.1.4.1 Substitution <strong>of</strong> Existing Substituents ....................................... 648<br />
17.4.1.4.1.1 Of Hydrogen .............................................................. 648<br />
17.4.1.4.1.2 Of Bromine ............................................................... 648
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