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


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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




The Chemists



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


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


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


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


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


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


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


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


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


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


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


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


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


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



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


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


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


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


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




The Chemistry



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



The “Father” of Russian Organic Chemistry



Structural theory of organic chemistry





Empirical rules that are still taught



Organozinc chemistry



Organozinc chemistry



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


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


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.


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


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.


Carbocation chemistry

  • S.S. Nametkin

    • Liebigs Ann. Chem. 1923, 432, 207.

  • I.N. Nazarov

    • Zh. Izv. Akad. Nauk SSSR Otd. Khim. Nauk 1942, 200.
      • prototypical example of a conrotatory electrocyclic reaction


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.


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.


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.


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.


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..


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.


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)


Some textbooks, etc.

  • N. Ya. Demyanov

    • Organic Chemistry (3rd. edition: Moscow, 1944)

  • A.E. Chichibabin

    • Organic Chemistry (Moscow, 1917; went through many editions)


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


The speaker





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