Table Of Content

VII Volume Editor’s Preface Thisvolume of Scienceof Synthesis is concernedwith thechemistry of nitrogenfunc- tionalities bonded to sp3-hybridized carbon atoms of alkyl groups or, in some cases, to sp2-hybridizedcarbonatomsofaryl,vinyl,oracylgroups.Themethodstopreparethecor- responding compounds withsuchnitrogenfunctionalities areveryimportantandmani- fold,andthuscannotbesummarizedinonevolumealone.Therefore,amines,ammonium salts, haloamines, hydroxylamines, hydrazines, triazanes, and tetrazanes are covered in Volume 40 of Science of Synthesis, whereas nitro-, nitroso-, and azidoalkanes, N-nitro- andN-nitrosoamines,azo,azoxy,andaliphaticdiazoniumcompounds,alkyltriazenesand -tetrazenes,andN,N-dihaloaminesarediscussed inVolume41.Severalrepresentativesof theseproductclasseshavebeenknownformorethan100years.Inrecentyears,however, new methods of synthesis or significant improvements to known reactions have been reported for all product classes covered in Volume 41. Thus, this volume, like all other volumesofScienceofSynthesis,willhelpresearchchemists inindustryandacademia tounderstandandcreativelyapplytheextensiveknowledgeintheareaoforganicsynthesis. Iwouldliketothankall17authorsfortheirvaluablecontributions,whichrepresent themajorpartofthiswork.Inparticular,theirpatienceinconnectionwithmyquestions andspecialwishesshouldbementioned.Furthermore,Iamgratefulanddeeplyimpressed by the professional work of the competent team at the editorial office of Thieme in Stuttgart.SuchavolumeofScienceofSynthesiscannotbeproducedwithouttheengage- mentoftheeditorialstafftomovetheprojectahead.Iamalsothankfultomyco-workers atChemnitzUniversityofTechnology,whosupportedmemanytimes.Finally,Iamgrate- ful to Dr. Joe P. Richmond, who convinced me some time ago that editing this volume would be a worthwhile undertaking. He also helped me at the planning stage of this volume,andthushecatalyzedthefirststeps,whicharealwaysthemostcritical. VolumeEditor KlausBanert Chemnitz,November2009 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG IX Volume 41: Nitro, Nitroso, Azo, Azoxy, and Diazonium Compounds, Azides, Triazenes, and Tetrazenes Preface .................................................................... V VolumeEditor’sPreface .................................................. VII Table ofContents ......................................................... XI Introduction K. Banert .................................................................. 1 41.1 Product Class 1:Nitroalkanes R.A. AitkenandK. M.Aitken .............................................. 9 41.2 Product Class 2:Nitrosoalkanes andNitroso Acetals(N,N-Dialkoxyamines) H.-U. Reissig,B. Dugovic(cid:1),andR.Zimmer .................................. 259 41.3 ProductClass3: N-Nitroamines U. Jahn .................................................................... 371 41.4 Product Class 4:N-Nitrosoamines M.M. K.Boysen ........................................................... 437 41.5 Product Class 5:Aliphatic AzoxyCompounds (Aliphatic Diazene Oxides) M.M. K.Boysen ........................................................... 449 41.6 Product Class 6:Aliphatic AzoCompounds S.Kempa,L. Wallach,andK. Rück-Braun ................................... 459 41.7 Product Class 7:Diazonium Compounds S.Kubik ................................................................... 507 41.8 Product Class 8:Azidoalkanes S.Bräse,B. Lesch, andV. Zimmermann .................................... 543 41.9 Product Class 9:Alkyltriazenes N.Jung andS.Bräse ....................................................... 613 41.10 Product Class 10: Alkyltetrazenes N.Jung andS.Bräse ....................................................... 641 41.11 Product Class 11: N,N-Dihaloamines S.J. Collier andW.Xiang .................................................. 651 Keyword Index ............................................................ 681 Author Index .............................................................. 721 Abbreviations ............................................................. 765 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG XI Table of Contents Introduction K. Banert Introduction ............................................................... 1 41.1 Product Class 1:Nitroalkanes R.A. AitkenandK. M.Aitken 41.1 Product Class 1:Nitroalkanes .............................................. 9 41.1.1 Synthesisof Product Class 1 ................................................ 9 41.1.1.1 Synthesisby Substitution ................................................... 9 41.1.1.1.1 Method 1: Substitution ofHydrogen UsingNitric Acid .................. 9 41.1.1.1.1.1 Variation 1: UsingDilute Nitric Acid ..................................... 9 41.1.1.1.1.2 Variation 2: UsingConcentrated orFuming Nitric Acid ................... 10 41.1.1.1.1.3 Variation 3: UsingNitric Acid with SulfuricAcid .......................... 12 41.1.1.1.1.4 Variation 4: UsingNitric Acid with Acetic Acid ........................... 13 41.1.1.1.1.5 Variation 5: UsingNitric Acid inIonic Liquids ............................ 13 41.1.1.1.1.6 Variation 6: UsingNitric Acid intheGas Phase .......................... 13 41.1.1.1.1.7 Variation 7: UsingNitric Acid with Oxygen andHalogens intheGas Phase ............................................ 14 41.1.1.1.2 Method 2: Substitution ofHydrogen UsingMetalNitrates .............. 15 41.1.1.1.2.1 Variation 1: UsingCopper(II) orManganese(II) Nitrates .................. 15 41.1.1.1.2.2 Variation 2: UsingAluminumTrinitrate .................................. 15 41.1.1.1.3 Method 3: Substitution ofHydrogen UsingSulfuric Acid and AmmoniumNitrate ......................................... 15 41.1.1.1.4 Method 4: Substitution ofHydrogen UsingNitrogen Dioxide ........... 15 41.1.1.1.4.1 Variation 1: Without AdditionalReagents ................................ 15 41.1.1.1.4.2 Variation 2: WithOxygen ................................................ 16 41.1.1.1.4.3 Variation 3: WithHydrogen Peroxide .................................... 17 41.1.1.1.5 Method 5: Substitution ofHydrogen UsingSodium Nitrite and Silver(I) Nitrate .............................................. 17 41.1.1.1.6 Method 6: Substitution ofHydrogen UsingAlkyl Nitrites ............... 17 41.1.1.1.6.1 Variation 1: Without AdditionalReagents ................................ 17 41.1.1.1.6.2 Variation 2: With3-Methylbutyl Nitrite andButyllithium ................. 18 41.1.1.1.7 Method 7: Substitution ofHydrogen Using AlkylNitrates witha Base ................................... 18 41.1.1.1.8 Method 8: Substitution ofHydrogen Using 2,4,6-Trichloro-N-nitroaniline ................................ 20 41.1.1.1.9 Method 9: Substitution ofLithium ...................................... 20 41.1.1.1.10 Method 10: Substitution ofPotassium ................................... 20 41.1.1.1.11 Method 11: Substitution ofMagnesium .................................. 20 41.1.1.1.12 Method 12: Substitution ofMercury ..................................... 21 41.1.1.1.13 Method 13: Substitution ofa CarboxyGroup ............................ 21 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG XII TableofContents 41.1.1.1.14 Method 14: Substitution ofa CyanoGroup .............................. 22 41.1.1.1.15 Method 15: Substitution ofChlorineUsingSodium Nitrite ............... 22 41.1.1.1.15.1 Variation 1: Without AdditionalReagents ................................ 23 41.1.1.1.15.2 Variation 2: WithUrea .................................................. 23 41.1.1.1.15.3 Variation 3: WithBenzene-1,3,5-triol .................................... 24 41.1.1.1.16 Method 16: Substitution ofChlorineUsingPotassium Nitrite ............ 24 41.1.1.1.16.1 Variation 1: In thePresence ofa Base ................................... 24 41.1.1.1.16.2 Variation 2: WithCrown Ethers .......................................... 25 41.1.1.1.17 Method 17: Substitution ofChlorineUsingSilver(I) Nitrite ............... 25 41.1.1.1.17.1 Variation 1: Without AdditionalReagents ................................ 25 41.1.1.1.17.2 Variation 2: WithUrea .................................................. 26 41.1.1.1.18 Method 18: Substitution ofChlorineUsingMercury(I) Nitrite ............ 27 41.1.1.1.19 Method 19: Substitution ofChlorineUsing Polymer-Supported Nitrite .................................. 27 41.1.1.1.20 Method 20: Substitution ofBromineUsingSodium Nitrite ............... 27 41.1.1.1.20.1 Variation 1: Without AdditionalReagents ................................ 27 41.1.1.1.20.2 Variation 2: WithBenzene-1,2-diol ...................................... 29 41.1.1.1.20.3 Variation 3: WithBenzene-1,3,5-triol .................................... 29 41.1.1.1.20.4 Variation 4: WithUrea .................................................. 31 41.1.1.1.20.5 Variation 5: WithUrea andBenzene-1,3,5-triol .......................... 32 41.1.1.1.20.6 Variation 6: Witha Phase-Transfer Catalyst .............................. 34 41.1.1.1.20.7 Variation 7: WithanIonic Liquid ......................................... 34 41.1.1.1.21 Method 21: Substitution ofBromineUsingPotassium Nitrite ............ 34 41.1.1.1.22 Method 22: Substitution ofBromineUsingSilver(I) Nitrite ............... 35 41.1.1.1.23 Method 23: Substitution ofBromineUsingAmmonium Nitrites .......... 38 41.1.1.1.24 Method 24: Substitution ofBromineUsingPolymer-Supported Nitrite ... 39 41.1.1.1.25 Method 25: Substitution ofIodine UsingSodium Nitrite ................. 39 41.1.1.1.25.1 Variation 1: Without AdditionalReagents ................................ 40 41.1.1.1.25.2 Variation 2: WithBenzene-1,3,5-triol .................................... 41 41.1.1.1.25.3 Variation 3: WithUrea .................................................. 41 41.1.1.1.25.4 Variation 4: WithUrea andBenzene-1,3,5-triol .......................... 42 41.1.1.1.26 Method 26: Substitution ofIodine UsingSilver(I)Nitrite ................. 43 41.1.1.1.27 Method 27: Substitution ofIodine UsingAmmoniumNitrites ............ 46 41.1.1.1.28 Method 28: Substitution ofIodine UsingPolymer-Supported Nitrite ...... 46 41.1.1.1.29 Method 29: Substitution ofSulfates ..................................... 46 41.1.1.1.30 Method 30: Substitution ofSulfonates ................................... 47 41.1.1.1.31 Method 31: Substitution ofOxoniumTetrafluoroborates ................. 48 41.1.1.1.32 Method 32: Substitution ofNitrogen inAzoCompounds ................ 48 41.1.1.2 Synthesisby Oxidation Reactions ........................................... 49 41.1.1.2.1 Method 1: Oxidation ofa Primary AminoGroupUsingCaro’s Acid ..... 49 41.1.1.2.2 Method 2: Oxidation ofa Primary AminoGroupUsing Hypofluorous Acid .......................................... 49 41.1.1.2.3 Method 3: Oxidation ofa Primary AminoGroupUsing Organic Peroxides ........................................... 50 41.1.1.2.3.1 Variation 1: UsingDimethyldioxirane .................................... 50 41.1.1.2.3.2 Variation 2: Using tert-ButylHydroperoxide andChromium Silicalite ..... 52 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG TableofContents XIII 41.1.1.2.3.3 Variation 3: Using tert-ButylHydroperoxide andZirconium(IV) tert-Butoxide ................................................ 52 41.1.1.2.3.4 Variation 4: UsingOxaziridinium Salts ................................... 53 41.1.1.2.4 Method 4: Oxidation ofa Primary AminoGroupUsing Organic PeroxyAcids ....................................... 53 41.1.1.2.4.1 Variation 1: UsingPeracetic Acid ........................................ 53 41.1.1.2.4.2 Variation 2: Using3-Chloroperoxybenzoic Acid .......................... 54 41.1.1.2.5 Method 5: Oxidation ofa Primary AminoGroupUsingOzone .......... 55 41.1.1.2.6 Method 6: Oxidation ofanAzido GroupUsingHypofluorous Acid ...... 56 41.1.1.2.7 Method 7: Oxidation ofanAzido GroupUsingOzone anda Phosphine ............................................ 57 41.1.1.2.8 Method 8: Oxidation ofa Hydroxyamino Group UsingNitric Acid ....... 57 41.1.1.2.8.1 Variation 1: Without AdditionalReagents ................................ 57 41.1.1.2.8.2 Variation 2: WithAmmonium Nitrate .................................... 58 41.1.1.2.9 Method 9: Oxidation ofa Hydroxyamino Group Using Potassium PermanganateinSulfuric Acid ................... 58 41.1.1.2.10 Method 10: Oxidation ofa Nitroso GroupUsing Nitric Acid .............. 59 41.1.1.2.10.1 Variation 1: WithAmmonium Nitrate .................................... 59 41.1.1.2.10.2 Variation 2: WithAcetic Acid ............................................ 59 41.1.1.2.11 Method 11: Oxidation ofa Nitroso GroupUsing Hydrogen Peroxide ..... 59 41.1.1.2.11.1 Variation 1: Without AdditionalReagents ................................ 59 41.1.1.2.11.2 Variation 2: WithSulfuric Acid ........................................... 59 41.1.1.2.12 Method 12: Oxidation ofa Nitroso GroupUsing Manganese(VII) ......... 60 41.1.1.2.12.1 Variation 1: UsingPotassium PermanganateinAcetone ................. 60 41.1.1.2.12.2 Variation 2: UsingManganese(VII) Oxide ................................ 60 41.1.1.2.13 Method 13: Oxidation ofa Nitroso GroupUsing Chromium(VI) .......... 60 41.1.1.2.13.1 Variation 1: UsingChromium(VI) Oxide Alone ........................... 60 41.1.1.2.13.2 Variation 2: UsingChromium(VI) Oxide andAcetic Acid ................. 60 41.1.1.2.13.3 Variation 3: UsingChromium(VI) Oxide withAcetic andSulfuric Acids ........................................... 61 41.1.1.2.14 Method 14: Oxidation ofa Nitroso GroupUsing Lead(IV) Oxide .......... 62 41.1.1.2.15 Method 15: Oxidation ofa Nitroso GroupUsing Oxidizing Gases ......... 62 41.1.1.2.15.1 Variation 1: UsingAir .................................................... 62 41.1.1.2.15.2 Variation 2: UsingOxygen ............................................... 62 41.1.1.2.15.3 Variation 3: UsingNitrogen Dioxide/Dinitrogen Tetroxide ................ 62 41.1.1.2.16 Method 16: Oxidation ofa Nitroso GroupUsing OrganicPeroxy Acids ... 63 41.1.1.2.16.1 Variation 1: UsingTrifluoroperoxyacetic Acid ............................ 63 41.1.1.2.16.2 Variation 2: Using3-Chloroperoxybenzoic Acid .......................... 63 41.1.1.2.17 Method 17: Photochemical Oxidation ofa Nitroso Group ................ 64 41.1.1.2.18 Method 18: Oxidation ofa Nitroso GroupUsing Iodosylbenzene ......... 64 41.1.1.2.19 Method 19: Oxidation ofanOximeGroup UsingNitric Acid ............. 64 41.1.1.2.19.1 Variation 1: Without Other Reagents .................................... 64 41.1.1.2.19.2 Variation 2: WithSulfuric Acid ........................................... 64 41.1.1.2.20 Method 20: Oxidation ofanOximeGroup UsingPeroxysulfates .......... 65 41.1.1.2.20.1 Variation 1: UsingCaro’s Acid ........................................... 65 41.1.1.2.20.2 Variation 2: UsingOxone ................................................ 65 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG XIV TableofContents 41.1.1.2.21 Method 21: Oxidation ofanOximeGroup UsingHydrogen Peroxide with Urea andMethyltrioxorhenium(VII) Catalyst ................. 66 41.1.1.2.22 Method 22: Oxidation ofanOximeGroup UsingLead(IV) Acetate ....... 66 41.1.1.2.23 Method 23: Oxidation ofanOximeGroup with Potassium Permanganate ................................... 66 41.1.1.2.24 Method 24: Oxidation ofanOximeGroup withSodium Perborate ....... 67 41.1.1.2.25 Method 25: Oxidation ofanOximeGroup Using Organic PeroxyAcids ....................................... 67 41.1.1.2.25.1 Variation 1: UsingTrifluoroperoxyacetic Acid ............................ 67 41.1.1.2.25.2 Variation 2: Using3-Chloroperoxybenzoic Acid .......................... 70 41.1.1.2.26 Method 26: Oxidation ofanOximeGroup Using Dinitrogen Tetroxide ........................................ 71 41.1.1.2.27 Method 27: Enzymatic Oxidation ofanOximeGroup .................... 71 41.1.1.3 Synthesisby AdditionReactions ............................................. 71 41.1.1.3.1 Method 1: Oxidative Nitrosation ofanOximeGroup ................... 72 41.1.1.3.2 Method 2: Oxidative Nitration ofanOximeUsing Nitric Acid ........... 72 41.1.1.3.2.1 Variation 1: Without AdditionalReagents ................................ 72 41.1.1.3.2.2 Variation 2: Followed byHydrogen Peroxide ............................. 73 41.1.1.3.2.3 Variation 3: WithAcetic Acid,Followed by Hydrogen Peroxide ........... 73 41.1.1.3.3 Method 3: Oxidative Nitration ofanOximeUsing NitrogenOxides ..... 74 41.1.1.3.3.1 Variation 1: UsingNitrogen Dioxide/Dinitrogen Tetroxide ................ 74 41.1.1.3.3.2 Variation 2: UsingNitrogen Dioxide andMagnesium Sulfate ............. 74 41.1.1.3.3.3 Variation 3: UsingDinitrogen Pentoxide ................................. 75 41.1.1.3.4 Method 4: Oxidative Chlorination ofanOximeUsingChlorine .......... 76 41.1.1.3.4.1 Variation 1: UsingChlorineFollowed by Ozone .......................... 76 41.1.1.3.4.2 Variation 2: UsingChlorinewith Hydrochloric, Nitric, andAcetic Acids ............................................ 77 41.1.1.3.5 Method 5: Oxidative Chlorination ofanOxime UsingSodium Hypochlorite ................................. 77 41.1.1.3.6 Method 6: Oxidative Chlorination ofanOxime UsingSodium Chloride,Oxone, andAlumina ................ 77 41.1.1.3.7 Method 7: Oxidative Chlorination ofanOxime UsingHydrochloric Acid andHydrogen Peroxide ............ 78 41.1.1.3.8 Method 8: Oxidative Bromination ofanOxime UsingSodium Hypobromite Followedby Nitric Acid ......... 78 41.1.1.3.9 Method 9: Oxidative Bromination ofanOxime UsingN-Bromoacetamide ................................... 79 41.1.1.3.10 Method 10: Oxidative Bromination ofanOxime UsingN-Bromosuccinimide andPotassium Carbonate ....... 80 41.1.1.3.11 Method 11: Oxidative Bromination ofanOxime UsingSodium Bromide,Oxone, andAlumina ................ 81 41.1.1.3.12 Method 12: Oxidative Acetoxylation ofanOximeUsingLead(IV) Acetate, Hydrogen Peroxide,andSodium Nitrite ............ 81 41.1.1.3.13 Method 13: Additionof NitrousAcid toanAlkene ....................... 82 41.1.1.3.13.1 Variation 1: UsingSodium Nitrite andAcetic Acid ....................... 82 41.1.1.3.13.2 Variation 2: UsingSodium Nitrite andHydrochloric Acid ................. 82 41.1.1.3.14 Method 14: Additionof Tetranitromethane toanAlkene ................ 83 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG TableofContents XV 41.1.1.3.15 Method 15: Nitrofluorination ofanAlkene ............................... 84 41.1.1.3.15.1 Variation 1: UsingNitric andHydrofluoric Acids ......................... 84 41.1.1.3.15.2 Variation 2: UsingNitryl Fluoride ........................................ 85 41.1.1.3.15.3 Variation 3: UsingNitronium Tetrafluoroborate andPyridiniumFluoride ..................................... 85 41.1.1.3.16 Method 16: Nitrochlorination ofanAlkene .............................. 86 41.1.1.3.16.1 Variation 1: UsingNitrosyl Chloride ...................................... 86 41.1.1.3.16.2 Variation 2: UsingNitrosyl Chloride,Nitrogen Dioxide, andOxygen ................................................. 87 41.1.1.3.16.3 Variation 3: UsingNitryl Chloride ........................................ 88 41.1.1.3.16.4 Variation 4: UsingNitrogen Dioxide andBoronTrifluoride ............... 89 41.1.1.3.16.5 Variation 5: UsingNitrogen Dioxide andChlorine ........................ 89 41.1.1.3.16.6 Variation 6: UsingNitrogen Dioxide,Phosphorus Trichloride, andOxygen ................................................. 90 41.1.1.3.17 Method 17: Nitrobromination ofanAlkene .............................. 90 41.1.1.3.17.1 Variation 1: UsingSodium Nitrite, Mercury(II) Chloride,andBromine .... 90 41.1.1.3.17.2 Variation 2: UsingNitrosyl Bromide ...................................... 91 41.1.1.3.17.3 Variation 3: UsingNitrogen Dioxide andBromine ........................ 92 41.1.1.3.17.4 Variation 4: UsingNitrogen Dioxide,Phosphorus Tribromide, andOxygen ................................................. 92 41.1.1.3.18 Method 18: Nitroiodination ofanAlkene ................................ 92 41.1.1.3.18.1 Variation 1: UsingSilver(I) Nitrite andIodine ............................ 92 41.1.1.3.18.2 Variation 2: UsingNitrogen Dioxide andIodine .......................... 93 41.1.1.3.19 Method 19: Nitroacetamidation ofanAlkene ............................ 94 41.1.1.3.20 Method 20: Nitronitrosation ofanAlkene (Synthesis ofc-Nitrosites) ..... 94 41.1.1.3.20.1 Variation 1: UsingSodium Nitrite andSulfuric Acid ...................... 95 41.1.1.3.20.2 Variation 2: UsingSodium Nitrite andHydrochloric Acid ................. 96 41.1.1.3.20.3 Variation 3: UsingSodium Nitrite andAcetic Acid ....................... 96 41.1.1.3.20.4 Variation 4: UsingSodium Nitrite andPhosphoric Acid .................. 97 41.1.1.3.20.5 Variation 5: UsingNitric Oxide with Catalysts ............................ 97 41.1.1.3.20.6 Variation 6: UsingNitric Oxide with Air .................................. 98 41.1.1.3.21 Method 21: 1,2-Dinitration of anAlkene ................................. 99 41.1.1.3.21.1 Variation 1: UsingPentyl Nitrite andAcetic Acid ......................... 99 41.1.1.3.21.2 Variation 2: UsingNitrogen Dioxide ..................................... 99 41.1.1.3.21.3 Variation 3: UsingNitrogen Dioxide andOxygen ......................... 101 41.1.1.3.22 Method 22: Nitrohydroxylation ofanAlkene ............................. 101 41.1.1.3.22.1 Variation 1: UsingNitric Acid ............................................ 101 41.1.1.3.22.2 Variation 2: UsingNitric andSulfuric Acids .............................. 102 41.1.1.3.22.3 Variation 3: UsingSodium Nitrite andAmmonium Cerium(IV) Nitrate .......................................... 102 41.1.1.3.22.4 Variation 4: UsingDinitrogen Trioxide ................................... 103 41.1.1.3.22.5 Variation 5: UsingNitrogen Dioxide ..................................... 103 41.1.1.3.22.6 Variation 6: UsingOrganic Nitrating Agents ............................. 104 41.1.1.3.23 Method 23: Nitromethoxylation ofanAlkene Using Tetranitromethane andMethanol ........................... 105 41.1.1.3.24 Method 24: Additionof aNitro Groupanda NitrateGroup toanAlkene ................................................ 105 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG XVI TableofContents 41.1.1.3.24.1 Variation 1: UsingNitric Acid ............................................ 105 41.1.1.3.24.2 Variation 2: UsingNitrogen Dioxide andOxygen ......................... 105 41.1.1.3.24.3 Variation 3: UsingDinitrogen Pentoxide ................................. 106 41.1.1.3.25 Method 25: Nitroacetoxylation ofan Alkene ............................. 108 41.1.1.3.25.1 Variation 1: UsingAcetyl Nitrate ......................................... 108 41.1.1.3.25.2 Variation 2: UsingNitric andSulfuric Acids Followed byAcetic Anhydride ......................................... 109 41.1.1.3.26 Method 26: Additionof aNitro Groupanda Perchlorate Group toanAlkene ................................................ 109 41.1.1.3.27 Method 27: Additionof aNitro GroupandanEthylSulfate Group toanAlkene ................................................ 110 41.1.1.3.28 Method 28: Conversion ofAlkenes intoa-Nitro Ketones ................. 110 41.1.1.3.28.1 Variation 1: UsingNitrogen Dioxide andOxygen inDimethyl Sulfoxide ....................................... 110 41.1.1.3.28.2 Variation 2: UsingChlorotrimethylsilane, Silver(I)Nitrate, andChromium(VI) Oxide .................................... 111 41.1.1.3.28.3 Variation 3: UsingChlorotrimethylsilane, Silver(I)Nitrate, andDimethyl Sulfoxide ..................................... 112 41.1.1.3.29 Method 29: Nitration ofSilyl Enol Ethers ................................ 112 41.1.1.3.29.1 Variation 1: UsingTetranitromethane .................................... 112 41.1.1.3.29.2 Variation 2: UsingNitronium Ethyl Sulfate ............................... 113 41.1.1.3.30 Method 30: Destructive Nitration ........................................ 113 41.1.1.4 Synthesisby Rearrangement orDisproportionation .......................... 115 41.1.1.4.1 Method 1: Rearrangement ofAlkylNitrates ............................ 115 41.1.1.4.2 Method 2: Disproportionation Reactions ................................ 116 41.1.1.5 Synthesiswith Retention oftheNitroGroup ................................ 116 41.1.1.5.1 Method 1: AlkylationofNitroalkanes with AlkylHalides ................ 117 41.1.1.5.1.1 Variation 1: WithFluoroalkanes .......................................... 117 41.1.1.5.1.2 Variation 2: WithChloroalkanes ......................................... 117 41.1.1.5.1.3 Variation 3: WithBromoalkanes ......................................... 119 41.1.1.5.1.4 Variation 4: WithIodoalkanes ........................................... 121 41.1.1.5.2 Method 2: AlkylationofNitroalkanes with Alkylammonium Salts ....... 122 41.1.1.5.3 Method 3: AlkylationofNitroalkanes with Alkyl(phenyl)iodonium Reagents ................................................... 122 41.1.1.5.4 Method 4: AlkylationofNitroalkanes with AlkylArenesulfonates ........ 123 41.1.1.5.5 Method 5: AlkylationofNitroalkanes with AlkylAryl Sulfones ........... 124 41.1.1.5.6 Method 6: AlkylationofNitroalkanes with Hydratesor Hemiacetals ofAldehydes ................................... 125 41.1.1.5.7 Method 7: AlkylationofNitroalkanes with AlkylAzides ................. 126 41.1.1.5.8 Method 8: AlkylationofNitroalkanes with anAlkylDifluoromethyl Nitrite ...................................................... 126 41.1.1.5.9 Method 9: Vinylation ofNitroalkanes ................................... 126 41.1.1.5.10 Method 10: Arylation ofNitroalkanes .................................... 127 41.1.1.5.11 Method 11: Allylation ofNitroalkanes .................................... 129 41.1.1.5.11.1 Variation 1: Nucleophilic Substitution .................................... 129 41.1.1.5.11.2 Variation 2: Palladium-Catalyzed Allylation ............................... 131 Science of Synthesis Original Edition Volume 41 © Georg Thieme Verlag KG

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