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It’s Not Just the Germans: Russian Contributions to the Development of Organic Chemistry

It’s Not Just the Germans: Russian Contributions to the Development of Organic Chemistry. David E. Lewis Department of Chemistry University of Wisconsin-Eau Claire University of Minnesota-Duluth, April 15, 2005. 1868. The Chemists.

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It’s Not Just the Germans: Russian Contributions to the Development of Organic Chemistry

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  1. It’s Not Just the Germans: Russian Contributions to the Development of Organic Chemistry David E. Lewis Department of Chemistry University of Wisconsin-Eau Claire University of Minnesota-Duluth, April 15, 2005

  2. 1868

  3. The Chemists

  4. Nikolai Nikolaevich Zinin (1812-1880)(Nikolay Nikolaeviq Zinin) • kandidat Kazan’ 1836 • Dr. Chem. St. Petersburg 1841 • study abroad (komandirovka) in western Europe 1838-1841 • intended for Zinin to learn technology • not intended for Zinin to learn “new” chemistry • year with Liebig in Giessen • Kazan’ University • Professor of Chemical Technology 1841-1848 • Medical-Surgical Academy, University of St. Petersburg • Professor of Chemistry 1848-1878 Justus von Liebig (1803-1873)

  5. Aleksandr Mikhailovich Butlerov(Butlerow) (1828-1886)(Aleksandr Mihayloviq Butlerov) • kandidat Kazan’ 1849 (entomology) • M. Chem. Kazan’ 1851 (under Klaus) • Dr. Chem. Moscow, 1854 (under Klaus) • study abroad (komandirovka) in western Europe 1857-1858, 1867-1868 • met Erlenmeyer and Kekulé • spent six months with Wurtz in Paris • not supposed to be a research trip • Kazan’ University • Professor of Chemical Technology 1851-1858 • Rector twice • University of St. Petersburg • Professor of Chemistry 1869-1880 Karl Karlovich Klaus (1796-1864) Charles-Adolphe Wurtz (1817-1884)

  6. Aleksandr Porfir’evich Borodin(Borodine) (1834-1887)(Aleksandr Porfir¡eviq Borodin) • kandidat St. Petersburg Medical-Surgical Academy 1855 • M.D. St. Petersburg Medical-Surgical Academy 1858 • study in western Europe 1859-1862 • travelled with Mendeleev • delegate to 1860 Karlsruhe conference • St. Petersburg Medical-Surgical Academy • Extraordinary Professor of Organic Chemistry 1862-1864 • Professor of Organic Chemistry 1864-1887

  7. Fedor Fedorevich Beil’shtein(Friedrich Konrad Beilstein)(1838-1906)(Fedor Fedoreviq Beyl¡wteyn) • 1853 sent to Germany to study • studied with Bunsen & Kekulé at Heidelberg • studied with Liebig at Munich • studied with Wöhler at Göttingen • Ph.D. Göttingen 1858 • University of Göttingen • Docent 1860 • Extraordinary Professor 1865 • Technical Institute, St. Petersburg • Chair in Chemistry, 1866-1906 • Editor, Zeitschrift für Chemie, 1865-1871 • with Hübner and Fittig Robert Wilhelm Eberhard Bunsen (1811-1899) Friedrich August Kekulé (1829-1896) Liebig Friedrich Wöhler (1800-1882)

  8. Vladimir Vasil’evich Markovnikov (Markownikoff) (1838-1904)(Vladimir Vasil¡eviq Markovnikov) • kandidat Kazan’ 1860 (economic science) • M. Chem. Kazan’ 1865 • Dr. Chem. Kazan’ 1869 • study abroad in western Europe 1865-1867 • studied with Kolbe at Leipzig • studied with Erlenmeyer in Heidelberg • Kazan’ University • docent 1867 • Extraordinary Professor of Chemistry 1868 • Professor of Chemistry 1869-1871 • Odessa University • Professor of Chemistry 1871-1873 • Moscow University • Professor of Chemistry 1873-1893 Adolph Wilhelm Hermann Kolbe (1818-1884)

  9. Aleksandr Mikhailovich Zaitsev(Saytzeff) (1841-1910)(Aleksandr Mihayloviq Zaycev) • diplom Kazan’ 1862 (economics) • kandidat Kazan’ 1865 • Ph.D. Leipzig 1866 • M. Chem. Kazan’ 1868 • Dr. Chem. Kazan’ 1870 • study abroad in western Europe 1862-1865 • studied with Kolbe at Marburg 1862-1864 • studied with Wurtz in Paris 1864-1865 • Kazan’ University • unpaid Laboratory Assistant 1865 • Assistant in Agronomy 1866-1868 • Extraordinary Professor of Chemistry 1869-1870 • Professor of Chemistry 1871-1910 Kolbe Wurtz

  10. Nikolai Aleksandrovich Menshutkin(1842-1907)(Nikolay Aleksandroviq Menwutkin) • kandidat St. Petersburg 1862 • M.Chem. St. Petersburg 1866 • Dr. Chem. St. Petersburg 1869 • study in western Europe 1863-1866 • study under Strecker in Tübingen • study under Wurtz in Paris • study under Kolbe in Leipzig • St. Petersburg University • Professor of Chemistry 1869-1902 • Chair in Organic Chemistry 1885-1902 • Petersburg Polytechnic Institute • Professor of Chemistry 1902-1907 Kolbe Wurtz

  11. Egor Egorevich Vagner (Georg Wagner) (1849-1903)(Egor Egoreviq Vagner) • kandidat Kazan’ 1874 • M. Chem. St. Petersburg 1885 • Dr. Chem. Warsaw 1888 • St. Petersburg University • Assistant under Menshutkin 1876-1882 • Novo-Aleksandriya Institute of Agrigulture and Forestry • Professor of Chemistry 1882-1886 • Warsaw University • Professor of Organic Chemistry 1886-1892 • Warsaw Polytechnic Institute • Professor of Organic Chemistry 1889-1903 • Dean of the Chemistry School 1889-1903

  12. Sergei Nikolaevich Reformatskii(Reformatsky) (1860-1934)(Sergey Nikolaeviq Reformatskiy) • graduated Kostroma Spiritual Seminary 1878 • kandidat Kazan’ 1882 • M. Chem. Kazan’ 1889 • Dr. Chem. Warsaw 1890 • study abroad in western Europe 1889-1890 • studied with Viktor Meyer at Heidelberg and Göttingen • studied with Wilhelm Ostwald at Leipzig • Kazan’ University • curator of museum 1882-1889 • Kiev University • Professor of Chemistry 1891-1934 • USSR Academy of Sciences • Corresponding Member 1928

  13. Aleksei Evgrafovich Favorskii(Favorsky) (1860-1945)(Aleksey Evgrafoviq Favorskiy) • kandidat St. Petersburg 1883 • M. Chem. St. Petersburg 1890 • Dr. Chem. St. Petersburg 1895 • St. Petersburg Technical Institute • Professor of Chemistry 1896-1907 • St. Petersburg University • Professor of Chemistry 1908-1929 • USSR Academy of Sciences • Associate Member 1921 • Academician 1929 • Institute of Organic Chemistry, USSR Academy of Science, St. Petersburg and Moscow. • Professor, 1929-1945

  14. Vyacheslav Evgen’evich Tishchenko(1861-1941)(Våqeslav Evgen¡eviq Tixenko) • M. Chem. St. Petersburg 1899 • Dr. Chem. St. Petersburg 1906 • travel abroad to report on technology • Chicago World’s Fair 1893 • Paris Exposition 1900 • St. Petersburg University • Professor 1901-1941

  15. Nikolai Dmitr’evich Zelinskii (Zelinsky) (1861-1853)(Nikolay Dmitrieviq Zelinskiy) • kandidat Odessa 1884 • M.Chem. Odessa 1889 • Dr. Chem. Odessa 1891 • study in western Europe 1885-1887 • Wislicenus at Leipzig • Viktor Meyer at Göttingen • Moscow University • Professor of Chemistry 1893-1953 • St. Petersburg Technical Institute • Professor of Chemistry 1911-1917 • USSR Academy of Sciences • Corresponding Member 1926 • Academician 1929 • Head, N.D. Zelinskii Institute 1934

  16. Nikolai Yakovlevich Demyanov(Demjanov) (1861-1938)(Nikolay Åkovleviq Dem¡ånov) • kandidat Moscow 1886 • M. Chem. Moscow 1895 • Dr. Chem. Moscow 1899 • Petrine Forestry and Agricultural Academy, Moscow • Assistant in Chemistry 1887-1893 • Adjunct Professor of Chemistry 1894-1898 • Professor of Chemistry 1898-1938 • Institute of Organic Chemistry, USSR Academy of Science • Director 1935-1938

  17. Nikolai Matveyevich Kizhner (Kishner) (1867-1935)(Nikolay Matveeviq Kijner) • kandidat Moscow 1890 • M. Chem. St. Petersburg 1895 • Dr. Chem. Moscow 1900 • Tomsk Technological Institute • Professor of Chemistry 1901-1913 • Shanyavskii Popular University, Moscow • Professor of Chemistry 1914-1917 • Aniline Trust Research Institute • Director 1918-1934 • Corresponding Member, USSR Academy of Sciences 1929-1934

  18. Aleksei Evgen’evich Chichibabin(Alexis Tchitchibabine) (1871-1945)(Aleksey Evgen¡eviq Qiqibabin) • kandidat Moscow 1892 • M. Chem. Moscow 1904 • Dr. Chem. St. Petersburg 1912 • Moscow University • Docent 1901, 1906-1908 • University of Warsaw • Adjunct Professor 1905-1906 • Moscow Higher Technical School • Director 1908-1929 • Dean, Chemistry Faculty (intermittent) 1909-1929 • Left Russia 1930 • worked with Tiffeneau at Hôtel Dieu; worked at Collège de France • Director, Scientific Departmenht, Kuhlman Co. 1930-1945; technical advisor, Schering and Rooseve;t Co. 1930-1945

  19. Lev Aleksandrovich Chugaev (Tschugaeff) (1873-1922)(Lev Aleksandroviq Qugaev) • M.Chem. Moscow 1903 • Dr. Chem. Moscow 1906 • Moscow University • Adjunct in Bacteriological Institute 1904-1908 • St. Petersburg University • Professor of Inorganic Chemistry 1908-1922

  20. Sergei Semenovich Nametkin(1876-1950)(Sergey Semenoviq Nametkin) • M. Chem. Moscow 1911 • Dr. Chem. Moscow 1916 • Moscow University • Extraordinary Professor 1910-1911, 1938-1950 • Moscow University Higher Women’s Courses • (Second Moscow University 1917) • Ordinary Professor 1911-1924 • Rector 1919-1924 • Moscow Institute of Fine Chemical Technology • Professor 1924-1938 • Moscow Mining Academy • (later Moscow Petroleum Institute) • Professor of organic chemistry and petrochemistry 1927-1950 • Rector 1919-1924

  21. Aleksandr Erminingel’dovich Arbuzov(Arbusow) (1877-1968)(Aleksandr Erminingel¡doviq Arbuzov) • diplom Kazan’ 1900 • M. Chem. Kazan’ 1905 • Dr. Chem. Warsaw 1914 • Novo-Aleksandriya Institute of Agriculture and Forestry • Assistant in Chemistry 1901-1905 • Professor of Chemistry 1906-1911 • Kazan’ University • Professor of Chemistry 1911-1930 • Deputy Dean, Physics-Mathematics Faculty 1922-1930 • Kazan’ Technical Institute, USSR Academy of Sciences • Professor and Director 1930-1944

  22. Ivan Nikolaevich Nazarov(1906-1957)(Ivan Nikolaeviq Nazarov) • kandidat Timiryazev Agricultural Academy 1931 • Dr. Chem. St. Petersburg (Leningrad) 1934 • Institute of Organic Chemistry, USSR Academy of Science • Associate 1934-1947 • Lomonosov Institute of Fine Chemicals (Moscow) • Professor 1947-1957 • USSR Academy of Sciences • Corresponding Member 1946 • Member 1953

  23. Butlerov Centenary, Kazan’ 1928

  24. The Chemistry

  25. Major Contributions • Zinin — the first Russian organic chemistry of note; “father of Russian organic chemistry” • structural theory of organic chemistry • synthesis using organozinc reagents • carbocation chemistry • chemistry of amines and other amino compounds • chemistry involving enols and enolates • textbooks of organic chemistry

  26. The “Father” of Russian Organic Chemistry N.N. Zinin Ann. Chem. Pharm.1840, 34, 186. Bull. Acad. Sci. St. Petersburg1842, 18. Bull. Phys.-Math. Acad. St. Petersburg1852, 348. Ann. Chem. Pharm.1842, 44, 283; 1844, 25, 361; 1853, 85, 328. “Even if Zinin had not done anything besides the conversion of nitrobenzene into aniline, his name would have, nevertheless, been inscribed in golden letters into the history of organic chemistry.” — August Wilhelm von Hofmann

  27. Structural theory of organic chemistry • A.M. Butlerov • Ann. Chem. Pharm.1859, 111, 5146. • V.V. Markovnikov • first synthesis of a cyclobutane • Ann. Chem. Pharm.1881, 208, 333. • first synthesis of cycloheptane • Comptes rend.1892, 110, 466; 115, 462.

  28. Empirical rules that are still taught • Markovnikov’s (Markownikoff’s) Rule (addition) • Ann. Chem. Pharm.1870, 133, 228. • Comptes rend.1875, 82, 668, 728, 776. • Zaitsev’s (Saytzeff’s) Rule (elimination) • Ann. Chem. Pharm.1875, 179, 296.

  29. Organozinc chemistry • A.M. Butlerov • Bull. Soc. Chim. Paris1863, 5, 582; 1864, 2, 106. • Jahresb.1863, 475; 1864, 496. • Ann. Chem. Pharm.1867, 144, 132 • A.M. Zaitsev • Ann. Chem. Pharm.1875, 175, 351, 374; 1877, 185, 148, 151, 175. • J. prakt. Chem.1885, 31, 319.

  30. Organozinc chemistry • E.E. Vagner • Zh. Russ. Khim. Obshch. Fiz. Obshch.1876, 8, 290. • Zh. Russ. Fiz.-Khim. Obshch. 1884, 16, 283. • Ann. Chem. Pharm.1875, 175, 351; 179, 302, 313. • Ber. Deut. chem. Ges.1894, 27, 2436. • S.N. Reformatskii • Ber. Deut. chem. Ges.1887, 20, 2110; 1895, 28, 2838, 2842, 3262.

  31. Redox chemistry • A.M. Butlerov • doctoral dissertation (1854) contains first report of osmium tetroxide oxidation of an alkene • A.P. Borodin • Z. Chem. 1861, 4, 5; 1869, 12, 342. • Ann. Chem. Pharm.1869, 121, 119

  32. Redox chemistry • A.M. Zaitsev • Ann. Chem. Pharm.1866, 139, 354; 1867, 144, 148. • Z. Chem., N.F.1869, 5, 551; 1870, 6, 105 • J. prakt. Chem., N.F.1871, 3, 76, 427. • E.E. Vagner (G. Wagner) • Deut. chem. Ges.1888, 21, 1230, 3343, 3347, 3356

  33. Redox chemistry • N.M. Kizhner (N. Kishner) • Zh. Russ. Fiz.-Khim. Obshch.1911, 43, 582. • N.D. Zelinskii (N.D. Zelinsky) • Ber. Deut. chem. Ges.1887, 20, 2026.

  34. Redox chemistry • V.E. Tishchenko • Zh. Russ. Fiz.-Khim. Obshch. 1906, 38, 355,482, 540, 547 • Chem. Zentr. 1906, II, 1309, 1552, 1555,1556. (c.f. Claisen, L. Ber. Deut. chem. Ges.1887, 20, 646.) • A.E. Arbuzov (A.E. Arbusow) • Zh. Russ. Fiz.-Khim. Obshch.1910, 42, 395, 549. • Chem. Zentr. 1910, 11, 453

  35. Carbocation chemistry • E.E. Vagner (G. Wagner) • Ber. Deut. chem. Ges.1899, 32, 2302; 1900, 33, 2121. • N. Ya. Demyanov (Demjanov) • Zh. Russ. Fiz.-Khim. Obshch. 1903, 35, 26; 1904, 36, 186. • Chem. Zentr. 1903, I, 828; 1904, I, 1214. • Ber. Deut. chem. Ges.1907, 40, 4393, 4961; 1908, 41, 43.

  36. Carbocation chemistry • S.S. Nametkin • Liebigs Ann. Chem.1923, 432, 207. • I.N. Nazarov • Zh. Izv. Akad. Nauk SSSR Otd. Khim. Nauk1942, 200. • prototypical example of a conrotatory electrocyclic reaction

  37. Enols and enolates:C—C bond formation • N.N. Zinin • Ann. Chem. Pharm.1840, 34, 186. • A.P. Borodin (Borodine) • Ber. Deut. chem. Ges.1873, 6, 973.

  38. Other C—C bond-forming reactions • A.E. Chichibabin (Chichibabine) • Ber. Deut. chem. Ges.1904, 37, 186, 850. • A.E. Favorskii (Favorsky) • Zh. Russ. Fiz.-Khim. Obshch.1900, 32, 652; 1905, 37, 643. • Chem. Zentr.1905, II, 1018.

  39. Amine and imine chemistry • A.E. Chichibabin • Zh. Russ. Fiz.-Khim. Obshch.1914, 46, 1216. • Zh. Russ. Fiz.-Khim. Obshch.1906, 37, 1229. • J. prakt. Chem.1924, 107, 122. • N.D. Zelinskii • Zh. Russ. Fiz-Khim. Obshch.1906, 38, 722; 1908, 40, 790.

  40. Base-promoted rearrangements • A.E. Favorskii (Favorsky) • Zh. Russ. Fiz.-Khim. Obshch.1887, 19, 414 • Ber. Deut. chem. Ges.1887, 20, 781. • J. prakt. Chem.1913, 88, 658.

  41. Other reactions • F.F. Beil’shtein (F.K. Beilstein) • halogenation of alkylbenzenes • Ann. Chem. Pharm.1866, 139, 331. • A.P. Borodin (Borodine) • first organic fluorine compound • Compt. rend.1862, 55, 552. • Z. Chem.1862, 5, 556. • Nuov. Cim. 1862, 15, 305. • Ann. Chem. Pharm.1863, 126, 58..

  42. Other reactions • N.A. Menshutkin • reaction rate studies in alcohols and amines • Z. phys. Chem.1890, 5, 589; 1891, 6, 41. • L.A. Chugaev (Tschugaeff) • Ber. Deut. chem. Ges.1899, 32, 3332.

  43. Some textbooks, etc. • A.M. Butlerov • Introduction to the Study of Organic Chemistry (Kazan’, 1861); Lehrbuch der organischen Chemie zur Einführung in das specielle Studien derselben (Leipzig, 1867) • F.F. Beil’shtein (F.K. Beilstein) • Beilsteins Handbuch der organischen Chemie (1881) • second edition 1886 • third edition 1893 • S.N. Reformatskii • A Beginner’s Course of Organic Chemistry (Kiev, 1891)

  44. Some textbooks, etc. • N. Ya. Demyanov • Organic Chemistry (3rd. edition: Moscow, 1944) • A.E. Chichibabin • Organic Chemistry (Moscow, 1917; went through many editions)

  45. Borodin: Late and Overdue Recognitions • Tony Award for Musical of the Year • Kismet, 1954 • Alexander Borodin, composer • Luther Davis, Robert Wright: librettists • George Forrest, lyricist • Charles Lederer, lyricist/producer • Named reaction • Borodin-Hunsdiecker reaction • Published by Borodin in 1861 • Patented by Heinz and Cläre Hunsdiecker in 1939 (published in Berichte 1942). • Borodin’s name slowly attached to it after the mid 1970’s

  46. The speaker

  47. Academic lineage

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