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SIMPLIFICATION OF THE GATTERMANN SYNTHESIS OF HYDROXY ALDEHYDES

Cite this: J. Am. Chem. Soc. 1923, 45, 10, 2373-2377
Publication Date (Print):October 1, 1923
https://doi.org/10.1021/ja01663a020
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This article is cited by 48 publications.

  1. Cecilia Blikstad, Käthe M. Dahlström, Tiina A. Salminen, and Mikael Widersten . Stereoselective Oxidation of Aryl-Substituted Vicinal Diols into Chiral α-Hydroxy Aldehydes by Re-Engineered Propanediol Oxidoreductase. ACS Catalysis 2013, 3 (12) , 3016-3025. DOI: 10.1021/cs400824h.
  2. Robert W. Bryant, Jr. and Robley Light, J.. Stipitatonic acid biosynthesis. Incorporation of [formyl- 14C]-3-methylorcylaldehyde and carbon-14-labeled stipitaldehydic acid, a new tropolone metabolite. Biochemistry 1974, 13 (7) , 1516-1522. DOI: 10.1021/bi00704a030.
  3. Alsoph H. Corwin, George G. Kleinspehn. Anomalous Displacements in the Pyrrole Series1. Journal of the American Chemical Society 1953, 75 (9) , 2089-2095. DOI: 10.1021/ja01105a020.
  4. Lloyd N. Ferguson. The Synthesis of Aromatic Aldehydes.. Chemical Reviews 1946, 38 (2) , 227-254. DOI: 10.1021/cr60120a002.
  5. Giovanny Carvalho dos Santos, Eliezer Fernando Oliveira, Francisco Carlos Lavarda, Luiz Carlos da Silva-Filho. Designing new quinoline-based organic photosensitizers for dye-sensitized solar cells (DSSC): a theoretical investigation. Journal of Molecular Modeling 2019, 25 (3) DOI: 10.1007/s00894-019-3958-y.
  6. Antonio Del Vecchio, Gianluca Destro, Frédéric Taran, Davide Audisio. Recent developments in heterocycle labeling with carbon isotopes. Journal of Labelled Compounds and Radiopharmaceuticals 2018, 61 (13) , 988-1007. DOI: 10.1002/jlcr.3666.
  7. Lu Yang, Li Wei, Jie-Ping Wan. Redox neutral [4+2] benzannulation of dienals and tertiary enaminones for benzaldehyde synthesis. Chemical Communications 2018, 54 (54) , 7475-7478. DOI: 10.1039/C8CC03514H.
  8. . Acylation. 2017,,, 569-592. DOI: 10.1002/9781119390541.ch8.
  9. Xianwei Sui, Linlin Ding, Zhenhua Gu. The palladium/norbornene-catalyzed ortho-silylmethylation reaction: a practical protocol for ortho-functionalized one-carbon homologation of aryl iodides. Chemical Communications 2016, 52 (97) , 13999-14002. DOI: 10.1039/C6CC08227K.
  10. Megharaja Holiyachi, Samundeeswari L. Shastri, Bahubali M. Chougala, Lokesh A. Shastri. Effects of Base for the Efficient Synthesis of 4-Formylcoumarins and 4-Formylcarbostyrils. Synthetic Communications 2015, 45 (8) , 1002-1008. DOI: 10.1080/00397911.2014.981754.
  11. Richard C. Burrell, John A. Easter, Michael P. Cassidy, Kevin W. Gillman, Richard E. Olson, Samuel J. Bonacorsi. Synthesis of carbon-14 and stable isotope labeled Avagacestat: a novel gamma secretase inhibitor for the treatment of Alzheimer's disease. Journal of Labelled Compounds and Radiopharmaceuticals 2014, 57 (10) , 600-605. DOI: 10.1002/jlcr.3224.
  12. Sakshi Shah, Baldev Singh. Catalyst-free, facile, and an efficient synthesis of α-aminonitriles employing Zn(CN)2 as an ecofriendly cyanating agent. Tetrahedron Letters 2012, 53 (2) , 151-156. DOI: 10.1016/j.tetlet.2011.10.154.
  13. WIlliam E. Truce. The Gattermann Synthesis of Aldehydes. 2011,,, 37-72. DOI: 10.1002/0471264180.or009.02.
  14. . Gattermann Aldehyde Synthesis. 2010,, DOI: 10.1002/9780470638859.conrr264.
  15. Jonathan Z. Ho, Charles S. Elmore, Matthew P. Braun. Synthesis of a 14 C-labeled FPTase inhibitor via a Pd-catalyzed cyanation with Zn( 14 CN) 2 and via bromo[ 14 C]acetic acid. Journal of Labelled Compounds and Radiopharmaceuticals 2008, 51 (12) , 399-403. DOI: 10.1002/jlcr.1545.
  16. Tse-Lok Ho, Mary Fieser, Louis Fieser. Zinc cyanide. 2006,, DOI: 10.1002/9780471264194.fos11277.
  17. Alfred Russell, Luther B. Lockhart. 2-Hydroxy-1-naphthaldehyde. 2003,,, 63-63. DOI: 10.1002/0471264180.os022.22.
  18. Harry Heaney. Zinc Cyanide. 2001,, DOI: 10.1002/047084289X.rz012.
  19. Wilford L. Mendelson, Stuart Hayden. Preparation of 2,4-Dihydroxybenzaldehyde by the Vilsmeier-Haack Reaction. Synthetic Communications 1996, 26 (3) , 603-610. DOI: 10.1080/00397919608003654.
  20. Henry N.C. Wong, Chang Rong Niu, Zhen Yang, Po Ming Hon, Hson Mou Chang, Chi Ming Lee. Regiospecific introduction of carbon-3 formyl group to 2,5-dialkyl-7-methoxy-benzo[b] furans : Synthesis of potential ligands for adenosine A1 receptors. Tetrahedron 1992, 48 (47) , 10339-10344. DOI: 10.1016/S0040-4020(01)88338-1.
  21. Zhen Yang, Po Ming Hon, Kuk Ying Chui, Zun Le Xu, Hson Mou Chang, Chi Ming Lee, Yu Xin Cui, Henry N.C. Wong, Chi Duen Poon, Bing M. Fung. Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen). Tetrahedron Letters 1991, 32 (18) , 2061-2064. DOI: 10.1016/S0040-4039(00)78908-8.
  22. Gerhard Nöhammer. Histochemical demonstration of primary amino groupswith 2-hydroxy-l-naphthaldehyde (HNA): Optimization of the methods. Acta Histochemica 1989, 86 (2) , 167-176. DOI: 10.1016/S0065-1281(89)80086-8.
  23. Wolfgang Uhl, Apostolos Kyriatsoulis. Gattermann. 1984,,, 68-70. DOI: 10.1007/978-3-663-02002-8_41.
  24. Stanley R. Sandler, Wolf Karo. ALDEHYDES. 1983,,, 180-205. DOI: 10.1016/B978-0-08-092556-1.50011-7.
  25. ROBERT C. SHEPPARD, BRIAN J. WILLIAMS. Acid-labile resin linkage agents for use in solid phase peptide synthesis. International Journal of Peptide and Protein Research 1982, 20 (5) , 451-454. DOI: 10.1111/j.1399-3011.1982.tb03067.x.
  26. E.G. Sundholm. Total syntheses of lichen xanthones. Tetrahedron 1978, 34 (5) , 577-586. DOI: 10.1016/0040-4020(78)80055-6.
  27. Eric Steiner, Julius Kalamar, Etienne Charollais, Théodore Posternak. Recherches sur la biochimie des champignons inférieurs IX. Synthèse de précurseurs marqués et biosynthèse de la phoenicine et de l'oosporéine. Helvetica Chimica Acta 1974, 57 (8) , 2377-2387. DOI: 10.1002/hlca.19740570810.
  28. B. N. Johri, H. J. Brodie, A. D. Allbutt, W. A. Ayer, H. Taube. A previously unknown antibiotic complex from the fungusCyathus helenae. Experientia 1971, 27 (7) , 853-853. DOI: 10.1007/BF02136907.
  29. J. S. Dave, George Kurian, A. P. Prajapati, R. A. Vora. Mesomorphic Behaviours of Schiff's Base Compounds: I: N,N′-Di(4-n-Alkoxy-l-Naphthylidene)-Benzidines. Molecular Crystals and Liquid Crystals 1971, 14 (3-4) , 307-317. DOI: 10.1080/15421407108084645.
  30. A. Kreutzberger. Die blausäurefreie Durchführung der Gattermannschen Aldehydsynthese. Archiv der Pharmazie 1969, 302 (11) , 828-838. DOI: 10.1002/ardp.19693021107.
  31. J.A. Ballantine, C.H. Hassall, B.D. Jones. The biosynthesis of phenols—XVII. Phytochemistry 1968, 7 (9) , 1529-1534. DOI: 10.1016/S0031-9422(00)88601-X.
  32. Christoph Grundmann, Reinhard Richter. Notiz über die Konstitution der isomeren Orcindialdehyde. Chemische Berichte 1966, 99 (8) , 2705-2706. DOI: 10.1002/cber.19660990843.
  33. Hans- J. Teuber, Günter Steinmetz. Reaktionen mit Nitrosodisulfonat, XXVI. 3-Hydroxy-naphthochinone-(1.2) und ihre farblosen Dimeren. Chemische Berichte 1965, 98 (3) , 666-684. DOI: 10.1002/cber.19650980304.
  34. Hans Gross, Alfred Rieche, Günter Matthey. Über α-Halogenäther, XIII. Neue Verfahren zur Darstellung von Phenolaldehyden. Chemische Berichte 1963, 96 (1) , 308-313. DOI: 10.1002/cber.19630960138.
  35. Minoru NAKAJIMA, Hiroshi FUKAMI, Kazuo KONISHI, Junichi ODA. Synthesis of Aromatic Carbonyl Compounds by Friedel-Crafts Reaction Using BF3 Catalyst. Agricultural and Biological Chemistry 1963, 27 (10) , 700-705. DOI: 10.1271/bbb1961.27.700.
  36. Alexander R. Surrey. Gattermann Aldehyde Synthesis. 1961,,, 112-114. DOI: 10.1016/B978-1-4832-3227-0.50050-X.
  37. Karl Freudenberg, José M. Alonso De Lama. ZUR KENNTNIS DER CATECHIN-GERBSTOFFE. Justus Liebigs Annalen der Chemie 1958, 612 (1) , 78-93. DOI: 10.1002/jlac.19586120109.
  38. J. S. Fitzgerald. The preparation of some methyl-substituted phenols and phenol alcohols. Journal of Applied Chemistry 1955, 5 (7) , 289-296. DOI: 10.1002/jctb.5010050701.
  39. S. R. Finn, G. J. Lewis, N. J. L. Megson. Formaldehyde condensations with phenol and its homologues. V. The methylol compounds of 3 : 5-dimethylphenol. Journal of the Society of Chemical Industry 1950, 69 (5) , 129-132. DOI: 10.1002/jctb.5000690501.
  40. H. Hellmann. Die Synthesen des Tryptophans. Angewandte Chemie 1949, 61 (9) , 352-357. DOI: 10.1002/ange.19490610903.
  41. B. B. Dey, S. Rajagopalan. Untersuchungen in der Reihe der Isochinoline. IV. Teil. Synthesen von Benzo-Isochinolonen und Untersuchung der Methoden, Isochinoline aus dem Naphthalinring herzustellen. Archiv der Pharmazie 1939, 277 (9) , 377-398. DOI: 10.1002/ardp.19392770902.
  42. Adolf Butenandt, Frank H. Stodola. Zur Kenntnis von α- und β-Leprosol. Justus Liebig's Annalen der Chemie 1939, 539 (1) , 40-56. DOI: 10.1002/jlac.19395390103.
  43. Sin'iti Kawai, Futoru Yoshimura, Koichi Ashino. 5-Aldehydo-acetovanillon, ein in seiner stark sauren Natur der Pikrinsäure ähnlicher Stoff. Berichte der deutschen chemischen Gesellschaft (A and B Series) 1938, 71 (2) , 324-328. DOI: 10.1002/cber.19380710222.
  44. Hans Meyer. Oxyoxoverbindungen. 1938,,, 958-1073. DOI: 10.1007/978-3-662-36309-6_8.
  45. Günther Schiemann, Wolfgang Winkelmüller. Über ein erstes Fluortyrosin und Fluorthyronin sowie kernfluorierte β-Phenyl-äthylamine. 3. Mitteilung über fluorierte Aminosäuren und ihre Abkömmlinge. Journal für Praktische Chemie 1932, 135 (3-5) , 101-127. DOI: 10.1002/prac.19321350303.
  46. Günther Schiemann. Über kern-fluorierte Amino-säuren (mitbearbeitet von W. Winkelmüller und W. Roselius.). Berichte der deutschen chemischen Gesellschaft (A and B Series) 1932, 65 (8) , 1435-1438. DOI: 10.1002/cber.19320650840.
  47. Hans Sickel. Indol und Indolabkömmlinge. 1930,,, 234-266. DOI: 10.1007/978-3-642-90827-9_6.
  48. Alexander St. Pfau. Zur Kenntnis der Flechtenbestandteile II. Die Konstitution der Barbatinsäure. Helvetica Chimica Acta 1928, 11 (1) , 864-876. DOI: 10.1002/hlca.192801101102.

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