It

1
Its 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

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1868
3
The Chemists
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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)
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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)
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Aleksandr Porfirevich Borodin(Borodine)
(1834-1887)(Aleksandr Porfireviq 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 Beilshtein(Friedrich Konrad
Beilstein) (1838-1906)(Fedor Fedoreviq
Beylwteyn)

• 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)
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Vladimir Vasilevich Markovnikov (Markownikoff)
(1838-1904)(Vladimir Vasileviq 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)
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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
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Nikolai Aleksandrovich Menshutkin(1842-1907)(Nik
olay 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
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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

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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

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Vyacheslav Evgenevich Tishchenko(1861-1941)(Våq
eslav Evgeneviq Tixenko)

• M. Chem. St. Petersburg 1899
• Dr. Chem. St. Petersburg 1906
• travel abroad to report on technology
• Chicago Worlds Fair 1893
• Paris Exposition 1900
• St. Petersburg University
• Professor 1901-1941

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Nikolai Dmitrevich 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

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Nikolai Yakovlevich Demyanov(Demjanov)
(1861-1938)(Nikolay Åkovleviq Demånov)

• 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

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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

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Aleksei Evgenevich Chichibabin(Alexis
Tchitchibabine) (1871-1945)(Aleksey Evgeneviq
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
  Roosevet Co. 1930-1945

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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

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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 Womens 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

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Aleksandr Erminingeldovich Arbuzov(Arbusow)
(1877-1968)(Aleksandr Erminingeldoviq 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

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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

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Butlerov Centenary, Kazan 1928
24
The Chemistry
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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

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The Father of Russian Organic Chemistry
N.N. Zinin
Ann. Chem. Pharm. 1840, 34, 186.
Bull. Acad. Sci. St. Petersburg 1842, 18. Bull.
Phys.-Math. Acad. St. Petersburg 1852, 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
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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.

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Empirical rules that are still taught

• Markovnikovs (Markownikoffs) Rule (addition)
• Ann. Chem. Pharm. 1870, 133, 228.
• Comptes rend. 1875, 82, 668, 728, 776.
• Zaitsevs (Saytzeffs) Rule (elimination)
• Ann. Chem. Pharm. 1875, 179, 296.

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Organozinc chemistry

• A.M. Butlerov
• Bull. Soc. Chim. Paris 1863, 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.

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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.

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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

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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

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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.

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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

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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.

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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

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Enols and enolatesCC bond formation

• N.N. Zinin
• Ann. Chem. Pharm. 1840, 34, 186.
• A.P. Borodin (Borodine)
• Ber. Deut. chem. Ges. 1873, 6, 973.

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Other CC 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.

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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.

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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.

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Other reactions

• F.F. Beilshtein (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..

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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.

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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. Beilshtein (F.K. Beilstein)
• Beilsteins Handbuch der organischen Chemie (1881)
• second edition 1886
• third edition 1893
• S.N. Reformatskii
• A Beginners Course of Organic Chemistry (Kiev,
  1891)

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Some textbooks, etc.

• N. Ya. Demyanov
• Organic Chemistry (3rd. edition Moscow, 1944)
• A.E. Chichibabin
• Organic Chemistry (Moscow, 1917 went through
  many editions)

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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).
• Borodins name slowly attached to it after the
  mid 1970s

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The speaker
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Academic lineage