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Balz–Schiemann reaction

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Balz, Günther; Schiemann, Günther (1927). "Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung" [Aromatic fluorine compounds. I. A new method for their preparation.].
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as a source of fluoride. An alternative methodology produces the fluoride salt of the diazonium compound. In this implementation, the diazotization is conducted with a solution of
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Laali, K. K., Herbert, M., Cushnyr, B., Bhatt, A., Terrano, D. (2001). "Benzylic oxidation of aromatics with cerium(IV) triflate; synthetic scope and mechanistic insight".
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Yu, Z., Lv, Y., Yu, C., Su, W. (March 2013). "Continuous flow reactor for Balz–Schiemann reaction: a new procedure for the preparation of aromatic fluorides".
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Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic".
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Sellers, C.; Suschitzky, H. (1968). "The use of arenediazonium hexafluoro-antimonates and -arsenates in the preparation of aryl fluorides".
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Rutherford, Kenneth G.; Redmond, William; Rigamonti, James (1961). "The Use of Hexafluorophosphoric Acid in the Schiemann Reaction".
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Becker H. G. O., Israel G. (1978). "Ionenpaareffekte bei der Photolyse und Thermolyse von Aryldiazonium-tetrafluoroboraten".
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proceeds without a promoter and is believed to generate highly unstable aryl cations (Ar), which abstract F from BF
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Swain, C. G.; Rogers, R. J. (1975). "Mechanism of formation of aryl fluorides from arenediazonium fluoborates".
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As a practical matter, the traditional Balz–Schiemann reaction consumes relatively expensive BF
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and involves isolation of the diazonium salt. Both aspects can be profitably modified. Other
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Chemical reaction in which an aromatic amine is transformed in aryl fluoride via a diazonium
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Roe A (1949). "Preparation of Aromatic Fluorine Compounds from Diazonium Fluoborates".
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tetrafluoroborate intermediate. This reaction is a traditional route to
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4-Fluorotoluene is made in ~89% yield by Balz-Schiemann reaction on
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Furuya, Takeru; Klein, Johannes E. M. N.; Ritter, Tobias (2010).
150:(ArCl, ArBr). However, while the Sandmeyer reaction involves a 151: 295:. This is then used as a precursor for 4-fluorobenzaldehyde, 571:
Advanced Organic Chemistry: Part B: Reactions and Synthesis
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Advanced Organic Chemistry: Part B: Reactions and Synthesis
112: 593: 335: 540: 678: 409:"C–F Bond Formation for the Synthesis of Aryl Fluorides" 573:(5th ed.). New York: Springer. p. 1030-1031. 190:
have been used in place of tetrafluoroborates, such as
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Journal of the Chemical Society, Perkin Transactions 1
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Erlenmeyer–Plöchl azlactone and amino-acid synthesis
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The traditional Balz–Schiemann reaction employs HBF
460:(5th ed.). New York: Springer. p. 1031. 2962:Divinylcyclopropane-cycloheptadiene rearrangement 622: 406: 214:without isolation of the diazonium intermediate. 4036: 569:Carey, Francis A.; Sundberg, Richard J. (2007). 456:Carey, Francis A.; Sundberg, Richard J. (2007). 272:The reaction is named after the German chemists 755: 3222:Thermal rearrangement of aromatic hydrocarbons 1856:Thermal rearrangement of aromatic hydrocarbons 648:Ullmann's Encyclopedia of Industrial Chemistry 3951:Lectka enantioselective beta-lactam synthesis 1211: 741: 373: 3730:Inverse electron-demand Diels–Alder reaction 1551:Heterogeneous metal catalyzed cross-coupling 480: 142:The reaction is conceptually similar to the 3072:Lobry de Bruyn–Van Ekenstein transformation 748: 734: 625:Journal of the Chemical Society C: Organic 170:to give the fluoroarene (ArF), along with 146:, which converts diazonium salts to other 3562:Petrenko-Kritschenko piperidone synthesis 3017:Fritsch–Buttenberg–Wiechell rearrangement 432: 369: 367: 3725:Intramolecular Diels–Alder cycloaddition 402: 400: 298: 126:and some related derivatives, including 14: 4037: 3745:Metal-centered cycloaddition reactions 3397:Debus–Radziszewski imidazole synthesis 1341:Bodroux–Chichibabin aldehyde synthesis 509:G. Schiemann; W. Winkelmüller (1943). 364: 3891:Diazoalkane 1,3-dipolar cycloaddition 3795:Vinylcyclopropane (5+2) cycloaddition 3700:Diazoalkane 1,3-dipolar cycloaddition 3472:Hurd–Mori 1,2,3-thiadiazole synthesis 2967:Dowd–Beckwith ring-expansion reaction 2134:Hurd–Mori 1,2,3-thiadiazole synthesis 1210: 1047:LFER solvent coefficients (data page) 729: 397: 304: 2702:Sharpless asymmetric dihydroxylation 1939:Methoxymethylenetriphenylphosphorane 2827:Allen–Millar–Trippett rearrangement 24: 3966:Nitrone-olefin (3+2) cycloaddition 3961:Niementowski quinazoline synthesis 3750:Nitrone-olefin (3+2) cycloaddition 3675:Azide-alkyne Huisgen cycloaddition 3537:Niementowski quinazoline synthesis 3292:Azide-alkyne Huisgen cycloaddition 2597:Meerwein–Ponndorf–Verley reduction 2149:Leimgruber–Batcho indole synthesis 25: 4066: 3790:Trimethylenemethane cycloaddition 3492:Johnson–Corey–Chaykovsky reaction 3357:Cadogan–Sundberg indole synthesis 3337:Bohlmann–Rahtz pyridine synthesis 3297:Baeyer–Emmerling indole synthesis 2104:Cadogan–Sundberg indole synthesis 1596:Johnson–Corey–Chaykovsky reaction 3886:Cook–Heilbron thiazole synthesis 3715:Hexadehydro Diels–Alder reaction 3542:Niementowski quinoline synthesis 3372:Cook–Heilbron thiazole synthesis 3317:Bischler–Möhlau indole synthesis 3227:Tiffeneau–Demjanov rearrangement 2857:Baker–Venkataraman rearrangement 2015:Horner–Wadsworth–Emmons reaction 1686:Mizoroki-Heck vs. Reductive Heck 1571:Horner–Wadsworth–Emmons reaction 1082:Neighbouring group participation 597:The Journal of Organic Chemistry 174:and nitrogen as the byproducts. 134: 3422:Fiesselmann thiophene synthesis 3252:Westphalen–Lettré rearrangement 3232:Vinylcyclopropane rearrangement 3062:Kornblum–DeLaMare rearrangement 2707:Epoxidation of allylic alcohols 2617:Noyori asymmetric hydrogenation 2552:Kornblum–DeLaMare rearrangement 2227:Gallagher–Hollander degradation 699: 672: 639: 3881:Chichibabin pyridine synthesis 3367:Chichibabin pyridine synthesis 3327:Blum–Ittah aziridine synthesis 3162:Ring expansion and contraction 1431:Cross dehydrogenative coupling 616: 587: 562: 534: 502: 474: 449: 177: 13: 1: 3851:Bischler–Napieralski reaction 3809:Heterocycle forming reactions 3462:Hemetsberger indole synthesis 3322:Bischler–Napieralski reaction 3237:Wagner–Meerwein rearrangement 3207:Sommelet–Hauser rearrangement 3187:Seyferth–Gilbert homologation 3052:Ireland–Claisen rearrangement 3047:Hofmann–Martius rearrangement 2807:2,3-sigmatropic rearrangement 2422:Corey–Winter olefin synthesis 2347:Barton–McCombie deoxygenation 1990:Corey–Winter olefin synthesis 1944:Seyferth–Gilbert homologation 1811:Seyferth–Gilbert homologation 357: 3956:Lehmstedt–Tanasescu reaction 3916:Gabriel–Colman rearrangement 3871:Bucherer carbazole synthesis 3866:Borsche–Drechsel cyclization 3846:Bernthsen acridine synthesis 3831:Bamberger triazine synthesis 3816:Algar–Flynn–Oyamada reaction 3527:Nazarov cyclization reaction 3392:De Kimpe aziridine synthesis 3347:Bucherer carbazole synthesis 3342:Borsche–Drechsel cyclization 3112:Nazarov cyclization reaction 3092:Meyer–Schuster rearrangement 3022:Gabriel–Colman rearrangement 2772:Wolffenstein–Böters reaction 2657:Reduction of nitro compounds 2507:Grundmann aldehyde synthesis 2312:Algar–Flynn–Oyamada reaction 1721:Olefin conversion technology 1716:Nozaki–Hiyama–Kishi reaction 1511:Gabriel–Colman rearrangement 1401:Claisen-Schmidt condensation 1346:Bouveault aldehyde synthesis 693:10.1016/j.tetlet.2012.12.084 7: 3931:Hantzsch pyridine synthesis 3710:Enone–alkene cycloadditions 3532:Nenitzescu indole synthesis 3452:Hantzsch pyridine synthesis 3417:Ferrario–Ackermann reaction 3067:Kowalski ester homologation 3032:Halogen dance rearrangement 2877:Benzilic acid rearrangement 2302:Akabori amino-acid reaction 2262:Von Braun amide degradation 2207:Barbier–Wieland degradation 2159:Nenitzescu indole synthesis 2139:Kharasch–Sosnovsky reaction 2030:Julia–Kocienski olefination 1934:Kowalski ester homologation 1631:Kowalski ester homologation 1606:Julia–Kocienski olefination 1361:Cadiot–Chodkiewicz coupling 1286:Aza-Baylis–Hillman reaction 1231:Acetoacetic ester synthesis 942:Dynamic binding (chemistry) 932:Conrotatory and disrotatory 907:Charge remote fragmentation 319:10.1002/0471264180.or005.04 286: 10: 4071: 3996:Robinson–Gabriel synthesis 3946:Kröhnke pyridine synthesis 3780:Retro-Diels–Alder reaction 3720:Imine Diels–Alder reaction 3507:Kröhnke pyridine synthesis 3122:Newman–Kwart rearrangement 3097:Mislow–Evans rearrangement 3007:Fischer–Hepp rearrangement 2952:Di-π-methane rearrangement 2732:Stephen aldehyde synthesis 2467:Eschweiler–Clarke reaction 2184:Williamson ether synthesis 1501:Fujiwara–Moritani reaction 1406:Combes quinoline synthesis 1371:Carbonyl olefin metathesis 1072:More O'Ferrall–Jencks plot 997:Grunwald–Winstein equation 967:Electron-withdrawing group 902:Catalytic resonance theory 568: 529:, vol. 2, p. 299 497:, vol. 2, p. 295 455: 267: 4006:Urech hydantoin synthesis 3986:Pomeranz–Fritsch reaction 3911:Fischer oxazole synthesis 3808: 3645:1,3-Dipolar cycloaddition 3635: 3617:Urech hydantoin synthesis 3587:Reissert indole synthesis 3572:Pomeranz–Fritsch reaction 3502:Knorr quinoline synthesis 3432:Fischer oxazole synthesis 3362:Camps quinoline synthesis 3282:1,3-Dipolar cycloaddition 3270: 3182:Semipinacol rearrangement 3157:Ramberg–Bäcklund reaction 3142:Piancatelli rearrangement 3082:McFadyen–Stevens reaction 2837:Alpha-ketol rearrangement 2785: 2592:McFadyen–Stevens reaction 2537:Kiliani–Fischer synthesis 2457:Elbs persulfate oxidation 2382:Bouveault–Blanc reduction 2342:Baeyer–Villiger oxidation 2280: 2197: 2174:Schotten–Baumann reaction 2077: 2050:Ramberg–Bäcklund reaction 1957: 1929:Kiliani–Fischer synthesis 1909: 1771:Ramberg–Bäcklund reaction 1756:Pinacol coupling reaction 1751:Piancatelli rearrangement 1646:Liebeskind–Srogl coupling 1496:Fujimoto–Belleau reaction 1219: 1213:List of organic reactions 1077:Negative hyperconjugation 822: 764: 89: 63:Organic Chemistry Portal 57: 32: 3981:Pictet–Spengler reaction 3896:Einhorn–Brunner reaction 3861:Boger pyridine synthesis 3755:Oxo-Diels–Alder reaction 3670:Aza-Diels–Alder reaction 3567:Pictet–Spengler reaction 3467:Hofmann–Löffler reaction 3457:Hegedus indole synthesis 3427:Fischer indole synthesis 3302:Bartoli indole synthesis 3257:Willgerodt rearrangement 3087:McLafferty rearrangement 2997:Ferrier carbocyclization 2812:2,3-Wittig rearrangement 2802:1,2-Wittig rearrangement 2642:Parikh–Doering oxidation 2632:Oxygen rebound mechanism 2297:Adkins–Peterson reaction 2189:Yamaguchi esterification 2129:Hegedus indole synthesis 2094:Bartoli indole synthesis 1965:Bamford–Stevens reaction 1881:Weinreb ketone synthesis 1841:Stork enamine alkylation 1616:Knoevenagel condensation 1486:Ferrier carbocyclization 1376:Castro–Stephens coupling 1002:Hammett acidity function 992:Free-energy relationship 937:Curtin–Hammett principle 922:Conformational isomerism 656:10.1002/14356007.a11_349 391:10.1002/cber.19270600539 350:10.1002/prac.19793210410 33:Balz-Schiemann reaction 3941:Knorr pyrrole synthesis 3876:Bucherer–Bergs reaction 3821:Allan–Robinson reaction 3800:Wagner-Jauregg reaction 3592:Ring-closing metathesis 3517:Larock indole synthesis 3497:Knorr pyrrole synthesis 3352:Bucherer–Bergs reaction 3217:Stieglitz rearrangement 3197:Skattebøl rearrangement 3167:Ring-closing metathesis 3027:Group transfer reaction 2992:Favorskii rearrangement 2932:Cornforth rearrangement 2862:Bamberger rearrangement 2767:Wolff–Kishner reduction 2587:Markó–Lam deoxygenation 2482:Fleming–Tamao oxidation 2477:Fischer–Tropsch process 2164:Oxymercuration reaction 2144:Knorr pyrrole synthesis 1970:Barton–Kellogg reaction 1876:Wagner-Jauregg reaction 1796:Ring-closing metathesis 1786:Reimer–Tiemann reaction 1776:Rauhut–Currier reaction 1691:Nef isocyanide reaction 1651:Malonic ester synthesis 1621:Knorr pyrrole synthesis 1556:High dilution principle 1491:Friedel–Crafts reaction 1426:Cross-coupling reaction 1351:Bucherer–Bergs reaction 1336:Blanc chloromethylation 1326:Blaise ketone synthesis 1301:Baylis–Hillman reaction 1296:Barton–Kellogg reaction 1271:Allan–Robinson reaction 1177:Woodward–Hoffmann rules 912:Charge-transfer complex 97:Balz–Schiemann reaction 68:balz-schiemann-reaction 18:Balz-Schiemann reaction 4050:Halogenation reactions 4045:Substitution reactions 3906:Feist–Benary synthesis 3680:Bradsher cycloaddition 3650:4+4 Photocycloaddition 3607:Simmons–Smith reaction 3552:Paternò–Büchi reaction 3412:Feist–Benary synthesis 3402:Dieckmann condensation 3152:Pummerer rearrangement 3132:Oxy-Cope rearrangement 3107:Myers allene synthesis 3057:Jacobsen rearrangement 2972:Electrocyclic reaction 2947:Demjanov rearrangement 2902:Buchner ring expansion 2872:Beckmann rearrangement 2852:Aza-Cope rearrangement 2847:Arndt–Eistert reaction 2822:Alkyne zipper reaction 2742:Transfer hydrogenation 2717:Sharpless oxyamination 2692:Selenoxide elimination 2577:Lombardo methylenation 2502:Griesbaum coozonolysis 2412:Corey–Itsuno reduction 2387:Boyland–Sims oxidation 2327:Angeli–Rimini reaction 1975:Boord olefin synthesis 1919:Arndt–Eistert reaction 1911:Homologation reactions 1711:Nitro-Mannich reaction 1626:Kolbe–Schmitt reaction 1436:Cross-coupling partner 1356:Buchner ring expansion 1276:Arndt–Eistert reaction 1042:Kinetic isotope effect 789:Rearrangement reaction 425:10.1055/s-0029-1218742 3765:Pauson–Khand reaction 3602:Sharpless epoxidation 3557:Pechmann condensation 3437:Friedländer synthesis 3387:Davis–Beirut reaction 3242:Wallach rearrangement 3212:Stevens rearrangement 3147:Pinacol rearrangement 3127:Overman rearrangement 3042:Hofmann rearrangement 3037:Hayashi rearrangement 3002:Ferrier rearrangement 2957:Dimroth rearrangement 2942:Curtius rearrangement 2937:Criegee rearrangement 2917:Claisen rearrangement 2907:Carroll rearrangement 2842:Amadori rearrangement 2832:Allylic rearrangement 2712:Sharpless epoxidation 2447:Dess–Martin oxidation 2372:Bohn–Schmidt reaction 2232:Hofmann rearrangement 2035:Kauffmann olefination 1958:Olefination reactions 1896:Wurtz–Fittig reaction 1731:Palladium–NHC complex 1611:Kauffmann olefination 1566:Homologation reaction 1416:Corey–House synthesis 1396:Claisen rearrangement 1192:Yukawa–Tsuno equation 1152:Swain–Lupton equation 1132:Spherical aromaticity 1067:Möbius–Hückel concept 852:Aromatic ring current 814:Substitution reaction 481:Flood, D. T. (1943). 299:Additional literature 200:hexafluoroantimonates 160:thermal decomposition 154:reagent/catalyst and 111:is transformed to an 52:Substitution reaction 3971:Paal–Knorr synthesis 3841:Barton–Zard reaction 3785:Staudinger synthesis 3735:Ketene cycloaddition 3705:Diels–Alder reaction 3685:Cheletropic reaction 3665:Alkyne trimerisation 3547:Paal–Knorr synthesis 3512:Kulinkovich reaction 3487:Jacobsen epoxidation 3407:Diels–Alder reaction 3202:Smiles rearrangement 3192:Sigmatropic reaction 3077:Lossen rearrangement 2927:Corey–Fuchs reaction 2892:Boekelheide reaction 2887:Bergmann degradation 2817:Achmatowicz reaction 2602:Methionine sulfoxide 2402:Clemmensen reduction 2362:Bergmann degradation 2292:Acyloin condensation 2257:Strecker degradation 2212:Bergmann degradation 2179:Ullmann condensation 2045:Peterson olefination 2020:Hydrazone iodination 2000:Elimination reaction 1901:Zincke–Suhl reaction 1821:Sonogashira coupling 1781:Reformatsky reaction 1741:Peterson olefination 1706:Nierenstein reaction 1636:Kulinkovich reaction 1451:Diels–Alder reaction 1411:Corey–Fuchs reaction 1391:Claisen condensation 1261:Alkyne trimerisation 1236:Acyloin condensation 1202:Σ-bishomoaromaticity 1162:Thorpe–Ingold effect 774:Elimination reaction 633:10.1039/J39680002317 515:-Fluorobenzoic Acid" 192:hexafluorophosphates 128:4-fluorobenzoic acid 3991:Prilezhaev reaction 3976:Pellizzari reaction 3655:(4+3) cycloaddition 3622:Van Leusen reaction 3597:Robinson annulation 3582:Pschorr cyclization 3577:Prilezhaev reaction 3307:Bergman cyclization 3262:Wolff rearrangement 3247:Weerman degradation 3137:Pericyclic reaction 3117:Neber rearrangement 3012:Fries rearrangement 2897:Brook rearrangement 2882:Bergman cyclization 2727:Staudinger reaction 2672:Rosenmund reduction 2662:Reductive amination 2627:Oppenauer oxidation 2417:Corey–Kim oxidation 2392:Cannizzaro reaction 2267:Weerman degradation 2242:Isosaccharinic acid 2154:Mukaiyama hydration 2010:Hofmann elimination 1995:Dehydrohalogenation 1980:Chugaev elimination 1801:Robinson annulation 1746:Pfitzinger reaction 1516:Gattermann reaction 1461:Wulff–Dötz reaction 1441:Dakin–West reaction 1366:Carbonyl allylation 1311:Bergman cyclization 1097:Kennedy J. P. Orton 1017:Hammond's postulate 987:Flippin–Lodge angle 957:Electromeric effect 882:Beta-silicon effect 867:Baker–Nathan effect 681:Tetrahedron Letters 610:10.1021/jo01070a089 556:10.1021/ja00837a019 158:intermediates, the 107:in which a primary 3740:McCormack reaction 3690:Conia-ene reaction 3522:Madelung synthesis 3312:Biginelli reaction 3102:Mumm rearrangement 2987:Favorskii reaction 2922:Cope rearrangement 2912:Chan rearrangement 2677:Rubottom oxidation 2607:Miyaura borylation 2572:Lipid peroxidation 2567:Lindgren oxidation 2547:Kornblum oxidation 2542:Kolbe electrolysis 2487:Fukuyama reduction 2397:Carbonyl reduction 2247:Marker degradation 2109:Diazonium compound 2099:Boudouard reaction 2078:Carbon-heteroatom 2005:Grieco elimination 1791:Rieche formylation 1736:Passerini reaction 1666:Meerwein arylation 1586:Hydroxymethylation 1481:Favorskii reaction 1381:Chan rearrangement 1316:Biginelli reaction 1241:Aldol condensation 1087:2-Norbornyl cation 1062:Möbius aromaticity 1057:Markovnikov's rule 952:Effective molarity 897:Bürgi–Dunitz angle 887:Bicycloaromaticity 378:Chemische Berichte 283:and Günther Balz. 259:]F → ArF + N 246:]F + NaF + 2 H 144:Sandmeyer reaction 101:Schiemann reaction 43:Günther Schiemann 4032: 4031: 4028: 4027: 4024: 4023: 4016:Wohl–Aue reaction 3660:6+4 Cycloaddition 3477:Iodolactonization 2797:1,2-rearrangement 2762:Wohl–Aue reaction 2682:Sabatier reaction 2647:Pinnick oxidation 2612:Mozingo reduction 2557:Leuckart reaction 2512:Haloform reaction 2427:Criegee oxidation 2407:Collins oxidation 2357:Benkeser reaction 2352:Bechamp reduction 2322:Andrussow process 2307:Alcohol oxidation 2217:Edman degradation 2124:Haloform reaction 2073: 2072: 2060:Takai olefination 2025:Julia olefination 1851:Takai olefination 1726:Olefin metathesis 1601:Julia olefination 1526:Grignard reaction 1506:Fukuyama coupling 1421:Coupling reaction 1386:Chan–Lam coupling 1256:Alkyne metathesis 1251:Alkane metathesis 1107:Phosphaethynolate 1012:George S. Hammond 972:Electronic effect 927:Conjugated system 809:Stereospecificity 804:Stereoselectivity 769:Addition reaction 758:organic reactions 687:(10): 1261–1263. 604:(12): 5149–5152. 544:J. Am. Chem. Soc. 527:Collected Volumes 520:Organic Syntheses 495:Collected Volumes 488:Organic Syntheses 419:(11): 1804–1821. 274:Günther Schiemann 227:hydrogen fluoride 210:salts such as SbF 172:boron trifluoride 164:tetrafluoroborate 162:of the diazonium 105:chemical reaction 99:(also called the 93: 92: 16:(Redirected from 4062: 4011:Wenker synthesis 4001:Stollé synthesis 3856:Bobbitt reaction 3826:Auwers synthesis 3770:Povarov reaction 3695:Cyclopropanation 3633: 3632: 3627:Wenker synthesis 3382:Darzens reaction 3332:Bobbitt reaction 3177:Schmidt reaction 2982:Enyne metathesis 2757:Whiting reaction 2752:Wharton reaction 2697:Shapiro reaction 2687:Sarett oxidation 2652:Prévost reaction 2462:Emde degradation 2272:Wohl degradation 2252:Ruff degradation 2222:Emde degradation 2119:Grignard reagent 2055:Shapiro reaction 2040:McMurry reaction 1907: 1906: 1871:Ullmann reaction 1836:Stollé synthesis 1826:Stetter reaction 1816:Shapiro reaction 1806:Sakurai reaction 1701:Negishi coupling 1681:Minisci reaction 1676:Michael reaction 1661:McMurry reaction 1656:Mannich reaction 1536:Hammick reaction 1531:Grignard reagent 1471:Enyne metathesis 1456:Doebner reaction 1446:Darzens reaction 1291:Barbier reaction 1281:Auwers synthesis 1208: 1207: 1182:Woodward's rules 1147:Superaromaticity 1137:Spiroaromaticity 1037:Inductive effect 1032:Hyperconjugation 1007:Hammett equation 947:Edwards equation 799:Regioselectivity 750: 743: 736: 727: 726: 720: 719: 716:10.1039/b008843i 703: 697: 696: 676: 670: 669: 643: 637: 636: 620: 614: 613: 591: 585: 584: 566: 560: 559: 538: 532: 530: 523: 506: 500: 498: 491: 478: 472: 471: 453: 447: 446: 436: 404: 395: 394: 385:(5): 1186–1190. 371: 353: 332: 282: 263: 251: 238:+ 2 HF + NaNO 138: 85: 70: 30: 29: 21: 4070: 4069: 4065: 4064: 4063: 4061: 4060: 4059: 4035: 4034: 4033: 4020: 3921:Gewald reaction 3804: 3631: 3612:Skraup reaction 3447:Graham reaction 3442:Gewald reaction 3273: 3266: 2788: 2781: 2737:Swern oxidation 2722:Stahl oxidation 2667:Riley oxidation 2622:Omega oxidation 2582:Luche reduction 2532:Jones oxidation 2497:Glycol cleavage 2492:Ganem oxidation 2437:Davis oxidation 2432:Dakin oxidation 2367:Birch reduction 2317:Amide reduction 2283: 2276: 2237:Hooker reaction 2199: 2193: 2081: 2079: 2069: 2065:Wittig reaction 1953: 1949:Wittig reaction 1924:Hooker reaction 1905: 1886:Wittig reaction 1861:Thorpe reaction 1846:Suzuki reaction 1831:Stille reaction 1766:Quelet reaction 1641:Kumada coupling 1591:Ivanov reaction 1581:Hydrovinylation 1561:Hiyama coupling 1521:Glaser coupling 1331:Blaise reaction 1321:Bingel reaction 1306:Benary reaction 1223: 1221: 1215: 1206: 1102:Passive binding 1022:Homoaromaticity 872:Baldwin's rules 847:Antiaromaticity 842:Anomeric effect 818: 760: 754: 724: 723: 704: 700: 677: 673: 666: 644: 640: 621: 617: 592: 588: 581: 567: 563: 539: 535: 525: 507: 503: 493: 483:"Fluorobenzene" 479: 475: 468: 454: 450: 405: 398: 372: 365: 360: 329: 301: 289: 276: 270: 262: 258: 254: 249: 245: 241: 237: 233: 220: 213: 205: 197: 185: 180: 169: 81: 66: 42: 28: 23: 22: 15: 12: 11: 5: 4068: 4058: 4057: 4055:Name reactions 4052: 4047: 4030: 4029: 4026: 4025: 4022: 4021: 4019: 4018: 4013: 4008: 4003: 3998: 3993: 3988: 3983: 3978: 3973: 3968: 3963: 3958: 3953: 3948: 3943: 3938: 3933: 3928: 3926:Hantzsch ester 3923: 3918: 3913: 3908: 3903: 3898: 3893: 3888: 3883: 3878: 3873: 3868: 3863: 3858: 3853: 3848: 3843: 3838: 3836:Banert cascade 3833: 3828: 3823: 3818: 3812: 3810: 3806: 3805: 3803: 3802: 3797: 3792: 3787: 3782: 3777: 3775:Prato reaction 3772: 3767: 3762: 3757: 3752: 3747: 3742: 3737: 3732: 3727: 3722: 3717: 3712: 3707: 3702: 3697: 3692: 3687: 3682: 3677: 3672: 3667: 3662: 3657: 3652: 3647: 3641: 3639: 3630: 3629: 3624: 3619: 3614: 3609: 3604: 3599: 3594: 3589: 3584: 3579: 3574: 3569: 3564: 3559: 3554: 3549: 3544: 3539: 3534: 3529: 3524: 3519: 3514: 3509: 3504: 3499: 3494: 3489: 3484: 3479: 3474: 3469: 3464: 3459: 3454: 3449: 3444: 3439: 3434: 3429: 3424: 3419: 3414: 3409: 3404: 3399: 3394: 3389: 3384: 3379: 3374: 3369: 3364: 3359: 3354: 3349: 3344: 3339: 3334: 3329: 3324: 3319: 3314: 3309: 3304: 3299: 3294: 3289: 3284: 3278: 3276: 3268: 3267: 3265: 3264: 3259: 3254: 3249: 3244: 3239: 3234: 3229: 3224: 3219: 3214: 3209: 3204: 3199: 3194: 3189: 3184: 3179: 3174: 3169: 3164: 3159: 3154: 3149: 3144: 3139: 3134: 3129: 3124: 3119: 3114: 3109: 3104: 3099: 3094: 3089: 3084: 3079: 3074: 3069: 3064: 3059: 3054: 3049: 3044: 3039: 3034: 3029: 3024: 3019: 3014: 3009: 3004: 2999: 2994: 2989: 2984: 2979: 2974: 2969: 2964: 2959: 2954: 2949: 2944: 2939: 2934: 2929: 2924: 2919: 2914: 2909: 2904: 2899: 2894: 2889: 2884: 2879: 2874: 2869: 2867:Banert cascade 2864: 2859: 2854: 2849: 2844: 2839: 2834: 2829: 2824: 2819: 2814: 2809: 2804: 2799: 2793: 2791: 2787:Rearrangement 2783: 2782: 2780: 2779: 2777:Zinin reaction 2774: 2769: 2764: 2759: 2754: 2749: 2747:Wacker process 2744: 2739: 2734: 2729: 2724: 2719: 2714: 2709: 2704: 2699: 2694: 2689: 2684: 2679: 2674: 2669: 2664: 2659: 2654: 2649: 2644: 2639: 2634: 2629: 2624: 2619: 2614: 2609: 2604: 2599: 2594: 2589: 2584: 2579: 2574: 2569: 2564: 2559: 2554: 2549: 2544: 2539: 2534: 2529: 2524: 2522:Hydrogenolysis 2519: 2514: 2509: 2504: 2499: 2494: 2489: 2484: 2479: 2474: 2472:Étard reaction 2469: 2464: 2459: 2454: 2449: 2444: 2439: 2434: 2429: 2424: 2419: 2414: 2409: 2404: 2399: 2394: 2389: 2384: 2379: 2377:Bosch reaction 2374: 2369: 2364: 2359: 2354: 2349: 2344: 2339: 2334: 2329: 2324: 2319: 2314: 2309: 2304: 2299: 2294: 2288: 2286: 2282:Organic redox 2278: 2277: 2275: 2274: 2269: 2264: 2259: 2254: 2249: 2244: 2239: 2234: 2229: 2224: 2219: 2214: 2209: 2203: 2201: 2195: 2194: 2192: 2191: 2186: 2181: 2176: 2171: 2166: 2161: 2156: 2151: 2146: 2141: 2136: 2131: 2126: 2121: 2116: 2114:Esterification 2111: 2106: 2101: 2096: 2091: 2085: 2083: 2075: 2074: 2071: 2070: 2068: 2067: 2062: 2057: 2052: 2047: 2042: 2037: 2032: 2027: 2022: 2017: 2012: 2007: 2002: 1997: 1992: 1987: 1982: 1977: 1972: 1967: 1961: 1959: 1955: 1954: 1952: 1951: 1946: 1941: 1936: 1931: 1926: 1921: 1915: 1913: 1904: 1903: 1898: 1893: 1891:Wurtz reaction 1888: 1883: 1878: 1873: 1868: 1863: 1858: 1853: 1848: 1843: 1838: 1833: 1828: 1823: 1818: 1813: 1808: 1803: 1798: 1793: 1788: 1783: 1778: 1773: 1768: 1763: 1761:Prins reaction 1758: 1753: 1748: 1743: 1738: 1733: 1728: 1723: 1718: 1713: 1708: 1703: 1698: 1693: 1688: 1683: 1678: 1673: 1668: 1663: 1658: 1653: 1648: 1643: 1638: 1633: 1628: 1623: 1618: 1613: 1608: 1603: 1598: 1593: 1588: 1583: 1578: 1576:Hydrocyanation 1573: 1568: 1563: 1558: 1553: 1548: 1546:Henry reaction 1543: 1538: 1533: 1528: 1523: 1518: 1513: 1508: 1503: 1498: 1493: 1488: 1483: 1478: 1473: 1468: 1463: 1458: 1453: 1448: 1443: 1438: 1433: 1428: 1423: 1418: 1413: 1408: 1403: 1398: 1393: 1388: 1383: 1378: 1373: 1368: 1363: 1358: 1353: 1348: 1343: 1338: 1333: 1328: 1323: 1318: 1313: 1308: 1303: 1298: 1293: 1288: 1283: 1278: 1273: 1268: 1263: 1258: 1253: 1248: 1246:Aldol reaction 1243: 1238: 1233: 1227: 1225: 1220:Carbon-carbon 1217: 1216: 1205: 1204: 1199: 1197:Zaitsev's rule 1194: 1189: 1184: 1179: 1174: 1169: 1164: 1159: 1154: 1149: 1144: 1142:Steric effects 1139: 1134: 1129: 1124: 1119: 1114: 1109: 1104: 1099: 1094: 1089: 1084: 1079: 1074: 1069: 1064: 1059: 1054: 1049: 1044: 1039: 1034: 1029: 1024: 1019: 1014: 1009: 1004: 999: 994: 989: 984: 979: 974: 969: 964: 959: 954: 949: 944: 939: 934: 929: 924: 919: 914: 909: 904: 899: 894: 889: 884: 879: 874: 869: 864: 859: 854: 849: 844: 839: 834: 829: 823: 820: 819: 817: 816: 811: 806: 801: 796: 794:Redox reaction 791: 786: 781: 779:Polymerization 776: 771: 765: 762: 761: 753: 752: 745: 738: 730: 722: 721: 710:(6): 578–583. 698: 671: 664: 638: 615: 586: 580:978-0387683546 579: 561: 550:(4): 799–800. 533: 501: 473: 467:978-0387683546 466: 448: 396: 362: 361: 359: 356: 355: 354: 344:(4): 579–586. 338:J. Prakt. Chem 333: 327: 300: 297: 288: 285: 269: 266: 265: 264: 260: 256: 252: 247: 243: 239: 235: 223:sodium nitrite 218: 211: 203: 195: 183: 179: 176: 167: 140: 139: 109:aromatic amine 91: 90: 87: 86: 79: 72: 71: 64: 60: 59: 55: 54: 49: 48:Reaction type 45: 44: 39: 35: 34: 26: 9: 6: 4: 3: 2: 4067: 4056: 4053: 4051: 4048: 4046: 4043: 4042: 4040: 4017: 4014: 4012: 4009: 4007: 4004: 4002: 3999: 3997: 3994: 3992: 3989: 3987: 3984: 3982: 3979: 3977: 3974: 3972: 3969: 3967: 3964: 3962: 3959: 3957: 3954: 3952: 3949: 3947: 3944: 3942: 3939: 3937: 3936:Herz reaction 3934: 3932: 3929: 3927: 3924: 3922: 3919: 3917: 3914: 3912: 3909: 3907: 3904: 3902: 3899: 3897: 3894: 3892: 3889: 3887: 3884: 3882: 3879: 3877: 3874: 3872: 3869: 3867: 3864: 3862: 3859: 3857: 3854: 3852: 3849: 3847: 3844: 3842: 3839: 3837: 3834: 3832: 3829: 3827: 3824: 3822: 3819: 3817: 3814: 3813: 3811: 3807: 3801: 3798: 3796: 3793: 3791: 3788: 3786: 3783: 3781: 3778: 3776: 3773: 3771: 3768: 3766: 3763: 3761: 3758: 3756: 3753: 3751: 3748: 3746: 3743: 3741: 3738: 3736: 3733: 3731: 3728: 3726: 3723: 3721: 3718: 3716: 3713: 3711: 3708: 3706: 3703: 3701: 3698: 3696: 3693: 3691: 3688: 3686: 3683: 3681: 3678: 3676: 3673: 3671: 3668: 3666: 3663: 3661: 3658: 3656: 3653: 3651: 3648: 3646: 3643: 3642: 3640: 3638: 3637:Cycloaddition 3634: 3628: 3625: 3623: 3620: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3600: 3598: 3595: 3593: 3590: 3588: 3585: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3565: 3563: 3560: 3558: 3555: 3553: 3550: 3548: 3545: 3543: 3540: 3538: 3535: 3533: 3530: 3528: 3525: 3523: 3520: 3518: 3515: 3513: 3510: 3508: 3505: 3503: 3500: 3498: 3495: 3493: 3490: 3488: 3485: 3483: 3482:Isay reaction 3480: 3478: 3475: 3473: 3470: 3468: 3465: 3463: 3460: 3458: 3455: 3453: 3450: 3448: 3445: 3443: 3440: 3438: 3435: 3433: 3430: 3428: 3425: 3423: 3420: 3418: 3415: 3413: 3410: 3408: 3405: 3403: 3400: 3398: 3395: 3393: 3390: 3388: 3385: 3383: 3380: 3378: 3377:Cycloaddition 3375: 3373: 3370: 3368: 3365: 3363: 3360: 3358: 3355: 3353: 3350: 3348: 3345: 3343: 3340: 3338: 3335: 3333: 3330: 3328: 3325: 3323: 3320: 3318: 3315: 3313: 3310: 3308: 3305: 3303: 3300: 3298: 3295: 3293: 3290: 3288: 3285: 3283: 3280: 3279: 3277: 3275: 3272:Ring forming 3269: 3263: 3260: 3258: 3255: 3253: 3250: 3248: 3245: 3243: 3240: 3238: 3235: 3233: 3230: 3228: 3225: 3223: 3220: 3218: 3215: 3213: 3210: 3208: 3205: 3203: 3200: 3198: 3195: 3193: 3190: 3188: 3185: 3183: 3180: 3178: 3175: 3173: 3172:Rupe reaction 3170: 3168: 3165: 3163: 3160: 3158: 3155: 3153: 3150: 3148: 3145: 3143: 3140: 3138: 3135: 3133: 3130: 3128: 3125: 3123: 3120: 3118: 3115: 3113: 3110: 3108: 3105: 3103: 3100: 3098: 3095: 3093: 3090: 3088: 3085: 3083: 3080: 3078: 3075: 3073: 3070: 3068: 3065: 3063: 3060: 3058: 3055: 3053: 3050: 3048: 3045: 3043: 3040: 3038: 3035: 3033: 3030: 3028: 3025: 3023: 3020: 3018: 3015: 3013: 3010: 3008: 3005: 3003: 3000: 2998: 2995: 2993: 2990: 2988: 2985: 2983: 2980: 2978: 2975: 2973: 2970: 2968: 2965: 2963: 2960: 2958: 2955: 2953: 2950: 2948: 2945: 2943: 2940: 2938: 2935: 2933: 2930: 2928: 2925: 2923: 2920: 2918: 2915: 2913: 2910: 2908: 2905: 2903: 2900: 2898: 2895: 2893: 2890: 2888: 2885: 2883: 2880: 2878: 2875: 2873: 2870: 2868: 2865: 2863: 2860: 2858: 2855: 2853: 2850: 2848: 2845: 2843: 2840: 2838: 2835: 2833: 2830: 2828: 2825: 2823: 2820: 2818: 2815: 2813: 2810: 2808: 2805: 2803: 2800: 2798: 2795: 2794: 2792: 2790: 2784: 2778: 2775: 2773: 2770: 2768: 2765: 2763: 2760: 2758: 2755: 2753: 2750: 2748: 2745: 2743: 2740: 2738: 2735: 2733: 2730: 2728: 2725: 2723: 2720: 2718: 2715: 2713: 2710: 2708: 2705: 2703: 2700: 2698: 2695: 2693: 2690: 2688: 2685: 2683: 2680: 2678: 2675: 2673: 2670: 2668: 2665: 2663: 2660: 2658: 2655: 2653: 2650: 2648: 2645: 2643: 2640: 2638: 2635: 2633: 2630: 2628: 2625: 2623: 2620: 2618: 2615: 2613: 2610: 2608: 2605: 2603: 2600: 2598: 2595: 2593: 2590: 2588: 2585: 2583: 2580: 2578: 2575: 2573: 2570: 2568: 2565: 2563: 2562:Ley oxidation 2560: 2558: 2555: 2553: 2550: 2548: 2545: 2543: 2540: 2538: 2535: 2533: 2530: 2528: 2527:Hydroxylation 2525: 2523: 2520: 2518: 2517:Hydrogenation 2515: 2513: 2510: 2508: 2505: 2503: 2500: 2498: 2495: 2493: 2490: 2488: 2485: 2483: 2480: 2478: 2475: 2473: 2470: 2468: 2465: 2463: 2460: 2458: 2455: 2453: 2452:DNA oxidation 2450: 2448: 2445: 2443: 2442:Deoxygenation 2440: 2438: 2435: 2433: 2430: 2428: 2425: 2423: 2420: 2418: 2415: 2413: 2410: 2408: 2405: 2403: 2400: 2398: 2395: 2393: 2390: 2388: 2385: 2383: 2380: 2378: 2375: 2373: 2370: 2368: 2365: 2363: 2360: 2358: 2355: 2353: 2350: 2348: 2345: 2343: 2340: 2338: 2335: 2333: 2332:Aromatization 2330: 2328: 2325: 2323: 2320: 2318: 2315: 2313: 2310: 2308: 2305: 2303: 2300: 2298: 2295: 2293: 2290: 2289: 2287: 2285: 2279: 2273: 2270: 2268: 2265: 2263: 2260: 2258: 2255: 2253: 2250: 2248: 2245: 2243: 2240: 2238: 2235: 2233: 2230: 2228: 2225: 2223: 2220: 2218: 2215: 2213: 2210: 2208: 2205: 2204: 2202: 2196: 2190: 2187: 2185: 2182: 2180: 2177: 2175: 2172: 2170: 2169:Reed reaction 2167: 2165: 2162: 2160: 2157: 2155: 2152: 2150: 2147: 2145: 2142: 2140: 2137: 2135: 2132: 2130: 2127: 2125: 2122: 2120: 2117: 2115: 2112: 2110: 2107: 2105: 2102: 2100: 2097: 2095: 2092: 2090: 2087: 2086: 2084: 2080:bond forming 2076: 2066: 2063: 2061: 2058: 2056: 2053: 2051: 2048: 2046: 2043: 2041: 2038: 2036: 2033: 2031: 2028: 2026: 2023: 2021: 2018: 2016: 2013: 2011: 2008: 2006: 2003: 2001: 1998: 1996: 1993: 1991: 1988: 1986: 1985:Cope reaction 1983: 1981: 1978: 1976: 1973: 1971: 1968: 1966: 1963: 1962: 1960: 1956: 1950: 1947: 1945: 1942: 1940: 1937: 1935: 1932: 1930: 1927: 1925: 1922: 1920: 1917: 1916: 1914: 1912: 1908: 1902: 1899: 1897: 1894: 1892: 1889: 1887: 1884: 1882: 1879: 1877: 1874: 1872: 1869: 1867: 1864: 1862: 1859: 1857: 1854: 1852: 1849: 1847: 1844: 1842: 1839: 1837: 1834: 1832: 1829: 1827: 1824: 1822: 1819: 1817: 1814: 1812: 1809: 1807: 1804: 1802: 1799: 1797: 1794: 1792: 1789: 1787: 1784: 1782: 1779: 1777: 1774: 1772: 1769: 1767: 1764: 1762: 1759: 1757: 1754: 1752: 1749: 1747: 1744: 1742: 1739: 1737: 1734: 1732: 1729: 1727: 1724: 1722: 1719: 1717: 1714: 1712: 1709: 1707: 1704: 1702: 1699: 1697: 1696:Nef synthesis 1694: 1692: 1689: 1687: 1684: 1682: 1679: 1677: 1674: 1672: 1671:Methylenation 1669: 1667: 1664: 1662: 1659: 1657: 1654: 1652: 1649: 1647: 1644: 1642: 1639: 1637: 1634: 1632: 1629: 1627: 1624: 1622: 1619: 1617: 1614: 1612: 1609: 1607: 1604: 1602: 1599: 1597: 1594: 1592: 1589: 1587: 1584: 1582: 1579: 1577: 1574: 1572: 1569: 1567: 1564: 1562: 1559: 1557: 1554: 1552: 1549: 1547: 1544: 1542: 1541:Heck reaction 1539: 1537: 1534: 1532: 1529: 1527: 1524: 1522: 1519: 1517: 1514: 1512: 1509: 1507: 1504: 1502: 1499: 1497: 1494: 1492: 1489: 1487: 1484: 1482: 1479: 1477: 1474: 1472: 1469: 1467: 1464: 1462: 1459: 1457: 1454: 1452: 1449: 1447: 1444: 1442: 1439: 1437: 1434: 1432: 1429: 1427: 1424: 1422: 1419: 1417: 1414: 1412: 1409: 1407: 1404: 1402: 1399: 1397: 1394: 1392: 1389: 1387: 1384: 1382: 1379: 1377: 1374: 1372: 1369: 1367: 1364: 1362: 1359: 1357: 1354: 1352: 1349: 1347: 1344: 1342: 1339: 1337: 1334: 1332: 1329: 1327: 1324: 1322: 1319: 1317: 1314: 1312: 1309: 1307: 1304: 1302: 1299: 1297: 1294: 1292: 1289: 1287: 1284: 1282: 1279: 1277: 1274: 1272: 1269: 1267: 1264: 1262: 1259: 1257: 1254: 1252: 1249: 1247: 1244: 1242: 1239: 1237: 1234: 1232: 1229: 1228: 1226: 1222:bond forming 1218: 1214: 1209: 1203: 1200: 1198: 1195: 1193: 1190: 1188: 1187:Y-aromaticity 1185: 1183: 1180: 1178: 1175: 1173: 1172:Walsh diagram 1170: 1168: 1165: 1163: 1160: 1158: 1157:Taft equation 1155: 1153: 1150: 1148: 1145: 1143: 1140: 1138: 1135: 1133: 1130: 1128: 1127:Σ-aromaticity 1125: 1123: 1120: 1118: 1115: 1113: 1110: 1108: 1105: 1103: 1100: 1098: 1095: 1093: 1090: 1088: 1085: 1083: 1080: 1078: 1075: 1073: 1070: 1068: 1065: 1063: 1060: 1058: 1055: 1053: 1052:Marcus theory 1050: 1048: 1045: 1043: 1040: 1038: 1035: 1033: 1030: 1028: 1027:Hückel's rule 1025: 1023: 1020: 1018: 1015: 1013: 1010: 1008: 1005: 1003: 1000: 998: 995: 993: 990: 988: 985: 983: 982:Evelyn effect 980: 978: 975: 973: 970: 968: 965: 963: 962:Electron-rich 960: 958: 955: 953: 950: 948: 945: 943: 940: 938: 935: 933: 930: 928: 925: 923: 920: 918: 915: 913: 910: 908: 905: 903: 900: 898: 895: 893: 890: 888: 885: 883: 880: 878: 877:Bema Hapothle 875: 873: 870: 868: 865: 863: 860: 858: 855: 853: 850: 848: 845: 843: 840: 838: 835: 833: 830: 828: 825: 824: 821: 815: 812: 810: 807: 805: 802: 800: 797: 795: 792: 790: 787: 785: 782: 780: 777: 775: 772: 770: 767: 766: 763: 759: 751: 746: 744: 739: 737: 732: 731: 728: 717: 713: 709: 702: 694: 690: 686: 682: 675: 667: 661: 657: 653: 649: 642: 634: 630: 627:: 2317–2319. 626: 619: 611: 607: 603: 599: 598: 590: 582: 576: 572: 565: 557: 553: 549: 546: 545: 537: 528: 522: 521: 516: 514: 505: 496: 490: 489: 484: 477: 469: 463: 459: 452: 444: 440: 435: 430: 426: 422: 418: 414: 410: 403: 401: 392: 388: 384: 381:(in German). 380: 379: 370: 368: 363: 351: 347: 343: 339: 334: 330: 324: 320: 316: 312: 308: 303: 302: 296: 294: 284: 280: 275: 253: 232: 231: 230: 228: 224: 215: 209: 201: 193: 189: 175: 173: 165: 161: 157: 153: 149: 145: 137: 133: 132: 131: 129: 125: 124:fluorobenzene 121: 117: 114: 110: 106: 102: 98: 88: 84: 80: 77: 74: 73: 69: 65: 62: 61: 56: 53: 50: 47: 46: 41:Günther Balz 40: 37: 36: 31: 19: 2977:Ene reaction 2337:Autoxidation 2198:Degradation 2089:Azo coupling 1866:Ugi reaction 1466:Ene reaction 1266:Alkynylation 1117:Polyfluorene 1112:Polar effect 977:Electrophile 892:Bredt's rule 862:Baird's rule 832:Alpha effect 707: 701: 684: 680: 674: 647: 641: 624: 618: 601: 595: 589: 570: 564: 547: 542: 536: 526: 518: 512: 504: 494: 486: 476: 457: 451: 416: 412: 382: 376: 341: 337: 310: 306: 290: 271: 242:→ [ArN 216: 181: 148:aryl halides 141: 100: 96: 94: 83:RXNO:0000127 78:ontology ID 58:Identifiers 38:Named after 1476:Ethenolysis 1122:Ring strain 1092:Nucleophile 917:Clar's rule 857:Aromaticity 293:p-toluidine 277: [ 208:nitrosonium 188:counterions 178:Innovations 4039:Categories 3760:Ozonolysis 3287:Annulation 2637:Ozonolysis 756:Topics in 665:3527306730 358:References 328:0471264180 307:Org. React 225:in liquid 3274:reactions 2789:reactions 2284:reactions 2200:reactions 2082:reactions 1224:reactions 413:Synthesis 120:diazonium 1167:Vinylogy 837:Annulene 784:Reagents 443:20953341 287:Examples 255:[ArN 116:fluoride 827:A value 434:2953275 313:: 193. 268:History 156:radical 103:) is a 662:  577:  464:  441:  431:  325:  198:) and 152:copper 118:via a 281:] 660:ISBN 575:ISBN 462:ISBN 439:PMID 417:2010 323:ISBN 234:ArNH 202:(SbF 113:aryl 95:The 712:doi 689:doi 652:doi 629:doi 606:doi 552:doi 429:PMC 421:doi 387:doi 346:doi 342:321 315:doi 194:(PF 76:RSC 4041:: 685:54 683:. 658:. 650:. 602:26 600:. 548:97 524:; 517:. 492:; 485:. 437:. 427:. 415:. 411:. 399:^ 383:60 366:^ 340:. 321:. 309:. 279:de 229:: 130:. 749:e 742:t 735:v 718:. 714:: 695:. 691:: 668:. 654:: 635:. 631:: 612:. 608:: 583:. 558:. 554:: 531:. 513:p 511:" 499:. 470:. 445:. 423:: 393:. 389:: 352:. 348:: 331:. 317:: 311:5 261:2 257:2 250:O 248:2 244:2 240:2 236:2 219:4 212:6 204:6 196:6 184:4 168:4 20:)

Index

Balz-Schiemann reaction
Substitution reaction
balz-schiemann-reaction
RSC
RXNO:0000127
chemical reaction
aromatic amine
aryl
fluoride
diazonium
fluorobenzene
4-fluorobenzoic acid
Balz–Schiemann reaction
Sandmeyer reaction
aryl halides
copper
radical
thermal decomposition
tetrafluoroborate
boron trifluoride
counterions
hexafluorophosphates
hexafluoroantimonates
nitrosonium
sodium nitrite
hydrogen fluoride
Günther Schiemann
de
p-toluidine
doi

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