Dave and the Dead Russians

Early Contributions by Russian Organic Chemists to the Development of the Discipline Nikolai Nikolaevich Zinin (1812-1880)

kandidat Kazan' 1836 Dr. Chem. St. Petersburg 1841 Study abroad in western Europe 1838-1841 • included a year with Liebig in Giessen • meant to be learning technology, not "new" chemistry Kazan' University • Professor of Chemical Technology 1841-1848 Medical-Surgical Academy, University of St. Petersburg • Professor of Chemistry 1848-1878 N. N. Zinin (1812-1880)

O CHO KCN

OH

Ann. Chem. Pharm. 1840, 34, 186-192.

NO2 NH2 NH3/H2S

Bull. Sci. Acad. St. Petersburg 1842, 18. Bull. Phys.-Math. Acad. St. Petersburg 1852, 348. Ann. Chem. Pharm. 1842, 44, 283-287; 1844, 52, 361-362; 1853, 85, 328-329. Aleksandr Mikhailovich Butlerov (1828-1886) kandidat Kazan' 1849 (entomology) M. Chem. Kazan' 1851 Dr. Chem. Moscow 1854 Study abroad 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 A. M. Butlerov (Butlerow) (1828-1886)

Structural Theory Ann. Chem. Pharm. 1859, 111, 5146.

Textbook Introduction to the Study of Organic Chemistry (Kazan', 1861).Lehrbuch der organischen Chemie zur Einführung in das specielle Studien derselben (Leipzig, 1867)

H C H3C ∆ 3 (CH3)2Zn/ C O H3C COH Cl H3C

Jahresb. 1863, 475; 1864, 496. Ann. Chem. Pharm. 1867, 144, 132. Aleksandr Mikhailovich Zaitsev (1841-1910) 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 1869-1871 • Professor of Chemistry 1871-1910 • served two terms as President of the Russian Physical- Chemical Society A. M. Zaitsev (Saytzeff) (1841-1910)

Zaitsev's Rule: Ann. Chem. Pharm. 1875, 179, 296-301.

R R HNO /H O S 3 2 S O R R Ann. Chem. Pharm. 1866, 139, 354-364; 1867, 144, 148-156.

Cl Na/Hg/Et2O C ROH RO HOAc Z. Chem., N.F. 1869, 5, 551-552; 1870, 6, 105-108 .J. prakt. Chem., N.F. 1871, 3, 76-88, 427.

Cl R' Cl R' R Zn R'I/Zn/Et O C O 2 R' OH C O 2 R' OH R R R R Ann. Chem. Pharm. 1875, 175, 351-374, 374-378; 1877, 185, 148-150, 151-169, 175-183. J. prakt. Chem. 1885, 31, 319-320. Vladimir Vasil’evich Markovnikov (1838-1904) kandidat Kazan' 1860 (economic science) M. Chem. Kazan' 1865 Dr. Chem. Kazan' 1869 Study abroad in Germany 1865-1867. • studied with Kolbe at Leipzig • studied with Erlenmeyer at Heidelberg Kazan' University • Docent in Chemistry 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 V. V. Markovnikov (Markownikoff) (1838-1904)

Markovnikov's Rule Ann. Chem. Pharm. 1870, 133, 228-259. Compt. rend. 1875, 82, 668-671, 728-730, 776-779.

Synthesis of HO C CO H 2 2 Ann. Chem. Pharm. 1881, 208, 333-349.

Synthesis of

Compt. rend. 1892, 110, 466-468; 115, 462-464. Sergei Nikolaevich Reformatskii (1860-1934) 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 (St. Vladimir) • Professor of Chemistry 1891-1934 Corresponding member, USSR Academy of Science 1928 S. N. Reformatskii (1860-1934)

Zn/Me2CO CO2Et Br CO 2Et OH

Zn/Me2CHCHO CO2Et Br CO 2Et OH Ber. Deut. chem. Ges. 1887, 20, 1210-1211; 1895, 28, 2838- 2841, 2842-2846, 3262-3265.

Textbook: A Beginner's Course of Organic Chemistry (Kiev, 1891) Egor Egorevich Vagner (1849-1903) kandidat Kazan' 1874 (juridicial science) M. Chem. St. Petersburg 1885 Dr. Chem. Warsaw 1888 St. Petersburg University • Assistant in Chemistry 1876-1882 (under Menshutkin) Novo-Aleksandriya Institute of Agriculture and Forestry • Professor of Chemistry 1882-1886 University of Warsaw • Professor of Chemistry 1886-1903 E. E. Vagner (Wagner) (1849-1903)

Et Zn OH CHO 2

Ann. Chem. Pharm. 1875, 175, 351-374; 1875, 179, 302-313, 313-325.

OH KMnO4 HO H2O

Ber. Deut. chem. Ges. 1888, 21, 1230-1240, 3343-3346, 3347-3355, 3356-3360.

H + OH OH

Ber. Deut. chem. Ges. 1899, 32, 2302-2325; 1900, 33, 2121-2125. Aleksandr Erminingel’dovich Arbuzov (1877-1968)

diplom Kazan' 1900 M. Chem. Kazan' 1905 Dr. Chem. Kazan' 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 A.E. Arbuzov (1877-1968)

PhO PhO MeI PhO P: O P Me PhO PhO

+PhOH+HI J. Russ. Phys. Chem. Soc. 1910, 42, 395-420, 549-561. Chem. Zentr. 1910, 11, 453-454. Nikolai Yakovlevich Demyanov (1861-1938) kandidat Moscow 1886 M. Chem. Moscow 1895 Dr. Chem. Moscow 1899 Petrine Forestry and Agricultural Academy, Moscow • Assistant 1887-1893 • Adjunct Professor 1894-1898 • Professor 1898-1938 Institute of Organic Chemistry, USSR Academy of Science • Director 1935-1938 N. Ya. Demyanov (N. J. Demjanov) (1861-1938)

NH2 OH HONO + OH

OH HONO NH2 OH +

J. Russ. Phys. Chem. Soc. 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.

Textbook • Organic Chemistry (3rd edition printed 1944) Nikolai Matveyevich Kizhner (1867-1935)

kandidat Moscow 1890 M. Chem. St. Petersburg 1895 Dr. Chem. Moscow 1900 Tomsk Technoological 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 N. M. Kizhner (Kishner) (1867-1935)

R R R NH NH KOH/∆ H O 2 2 NNH 2 H R R R

J. Russ. Phys. Chem. Soc. 1911, 43, 582. (c.f. Chem. Abstr. 1912, 6, 347). Aleksei Evgenievich Chichibabin (1871-1945)

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 • Professor 1908-1929 • Dean, Chemistry Faculty (intermittent) 1909-1929

Left Russia 1930 • worked with Tiffeneau at Hôtel Dieu • worked at Collège de France • Director, Scientific Department, Kuhlman Co. 1930-45 • technical advisor, Schering & Roosevelt Co. 1930-1945 A. E. Chichibabin (1871-1945)

NaNH2

N NNH2 J. Russ. Phys. Chem. Soc. 1914, 46, 1216.

RR NH3 R CHO ∆ R N J. Russ. Phys. Chem. Soc. 1906, 37, 1229. J. prakt. Chem. 1924, 107, 122.

OEt OEt RMgX H O EtO R 3 R CHO OEt OEt Ber. Deut. chem. Ges. 1904, 37, 186; 850. Nikolai Dmitrievich Zelinskii (1861-1953) kandidat Odessa 1884 M. Chem. Odessa 1889 Dr. Chem. Odessa 1891 Studied abroad 1885-1887 • studied with Wislicenus at Leipzig and V. Meyer at Göttingen Moscow University • Professor of Chemistry 1893-1953 St. Petersburg Polytechnical Institute • Professor of Chemistry 1911-1917 USSR Academy of Sciences • Corresponding Member 1926 • Academician 1929 • Head, N.D. Zelinskii Institute 1934 N. D. Zelinskii (Zelinsky) (1861-1953)

CN R R CHO +NH4Cl + KCN NH2 J. Russ. Phys. Chem. Soc. 1906, 38, 722; 1908, 40, 790.

Br 1) Br /P R 2 R 2) H O CO2H 2 CO2H

Ber. Deut. chem. Ges. 1887, 20, 2026. Lev Aleksandrovich Chugaev (1873-1922)

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 L A. Chugaev (Tschugaeff) (1873-1922)

1) NaOH/CS R 2 R OH 2) MeI 3) ∆

Ber. Deut. chem. Ges. 1899, 32, 3332.

Development of α-dioximes as reagents for Group VIIIB metals (e.g. dimethylglyoxime for nickel) Z. anorg. allgem. Chem. 1905, 46, 144. Nikolai Aleksandrovich Menshutkin (1842-1907) kandidat St. Petersburg 1862 M. Chem. St. Petersburg 1866 Dr. Chem. St. Petersburg 1869 Study abroad in western Europe 1863-1866 • studied with Strecker in Tübingen, Wurtz in Paris, Kolbe in Leipzig St. Petersburg University • Professor of Chemical Technology 1841-1848 Medical-Surgical Academy, University of St. Petersburg • Professor of Chemistry 1848-1878 N. A. Menshutkin (Menschutkin) (1842-1907) Reaction rate studies in alcohols and amines:

R1 R1 R2 N + RX R2 NR4 X R3 R3

Z. Phys. Chem. 1890, 5, 589; 1891, 6, 41. Aleksandr Porfir’evich Borodin (1834-1887) kandidat St. Petersburg Medical-Surgical Academy 1855 M.D. St. Petersburg Medical-Surgical Academy 1858 Study in western Europe 1859-1862 • frequently travelled with Mendeleev • delegate to Karlsruhe conference 1860 St. Petersburg Medical-Surgical Academy • Extraordinary Professor of Organic Chemistry 1862-1864 • Professor of Organic Chemistry 1864-1887 A. P. Borodin (Borodine) (1834-1887)

Br2 RCO2Ag R Br Z. Chem. 1861, 4, 5; 1869, 12, 342. Ann. Chem. Pharm. 1861, 119, 121.

R R CHO NaOH R CHO OH Ber. Deut. chem. Ges. 1873, 6, 982.

KHF COCl 2 COF Compt. rend. 1862, 55, 553. Z. Chem. 1862, 5, 576. Nuov. Cim. 1862, 15, 305. Ann. Chem. Pharm. 1863, 126, 58. Aleksei Evgrafovich Favorskii (1860-1945) kandidat St. Petersburg 1883 M. Chem. St. Petersburg 1891 Dr. Chem. St. Petersburg 1895 St. Petersburg Technical Institute • Professor of Chemistry 1896-1907 USSR Academy of Sciences • Associate Member 1921 • Academician 1929 A. E. Favorskii (Favorsky) (1860-1945)

R H

RCH2 CCH CCC RCHC C 3 H H J. Russ. Phys. Chem. Soc. 1887, 19, 414. Ber. Deut. chem. Ges. 1887, 20, 781.

R R RCCH+O RCC OH R R J. Russ Phys. Chem. Soc. 1900, 32, 652; 1905, 37, 643. Chem. Zentr. 1905, II, 1018.

O NaOH CO2H Br J. prakt. Chem. 1913, 88, 658. Vyacheslav Evgenievich Tishchenko (1861-1941)

Al(OEt) Ar O Ar Ar CHO 3 O J. Russ. Phys. Chem. Soc. 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. Ivan Nikolaevich Nazarov (1906-1957)

RR RR RR acid O OH O

Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1942, 200. Sergei Semenovich Nametkin (1876-1950)

R R

H

Liebigs Ann. Chem. 1923, 432, 207.