Dave and the Dead Russians

Early Contributions by Russian OrganicChemists to the Development of the

Discipline

Nikolai Nikolaevich Zinin(1812-1880)

kandidat Kazan' 1836Dr. 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)

CHOKCN

O

OH

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

NO2 NH3/H2SNH2

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' 1851Dr. 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 TheoryAnn. Chem. Pharm. 1859, 111, 5146.

TextbookIntroduction to the Study of Organic Chemistry

(Kazan', 1861).Lehrbuch der organischen Chemie zurEinführung in das specielle Studien derselben (Leipzig,1867)

CH3C

OCl

(CH3)2Zn/∆C OH

H3C

H3CH3C

Jahresb. 1863, 475; 1864, 496.Ann. Chem. Pharm. 1867, 144, 132.

Aleksandr Mikhailovich Zaitsev(1841-1910)

diplom Kazan' 1862 (economics)kandidat Kazan' 1865Ph.D. Leipzig 1866M. Chem. Kazan' 1868Dr. 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.

SR

RHNO3/H2O S

R

RO

Ann. Chem. Pharm. 1866, 139, 354-364; 1867, 144, 148-156.

CR O

Cl Na/Hg/Et2OR OHHOAc

Z. Chem., N.F. 1869, 5, 551-552; 1870, 6, 105-108.J. prakt. Chem., N.F. 1871, 3, 76-88, 427.

CR

OCl

ROH

R'R'

R2ZnC

RO

Cl

ROH

R'R'

R'I/Zn/Et2O

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' 1865Dr. 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 RuleAnn. Chem. Pharm. 1870, 133, 228-259.Compt. rend. 1875, 82, 668-671, 728-730, 776-779.

Synthesis of

CO2HHO2C

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 1878kandidat Kazan' 1882M. Chem. Kazan' 1889Dr. 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)

Br CO2Et

Zn/Me2COCO2Et

OH

Br CO2Et

Zn/Me2CHCHOCO2Et

OHBer. 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 1885Dr. Chem. Warsaw 1888

St. Petersburg University• Assistant in Chemistry 1876-1882 (under Menshutkin)

Novo-Aleksandriya Institute ofAgriculture and Forestry• Professor of Chemistry 1882-1886

University of Warsaw• Professor of Chemistry 1886-1903

E. E. Vagner (Wagner)(1849-1903)

CHO Et2Zn OH

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

KMnO4

H2OHO

OH

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' 1900M. Chem. Kazan' 1905Dr. 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)

MePPhO

PhOOP:

PhO

PhOPhO MeI

+ Ph OH + 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 1886M. Chem. Moscow 1895Dr. 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 ofScience• Director 1935-1938

N. Ya. Demyanov (N. J. Demjanov)(1861-1938)

HONONH2 OH

OH+

+HONONH2 OHOH

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 1890M. Chem. St. Petersburg 1895Dr. 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 Sciences1929-1934

N. M. Kizhner (Kishner)(1867-1935)

R

R H

HKOH/∆NNH2

R

RNH2NH2O

R

R

J. Russ. Phys. Chem. Soc. 1911, 43, 582.(c.f. Chem. Abstr. 1912, 6, 347).

Aleksei Evgenievich Chichibabin(1871-1945)

kandidat Moscow 1892M. Chem. Moscow 1904Dr. 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)

N

NaNH2

N NH2

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

CHORNH3

∆N

R

R R

J. Russ. Phys. Chem. Soc. 1906, 37, 1229.J. prakt. Chem. 1924, 107, 122.

EtOOEt

OEt

RMgXR

OEt

OEt

H3OCHOR

Ber. Deut. chem. Ges. 1904, 37, 186; 850.

Nikolai Dmitrievich Zelinskii(1861-1953)

kandidat Odessa 1884M. Chem. Odessa 1889Dr. 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)

R CHO + NH4Cl + KCN RCN

NH2

J. Russ. Phys. Chem. Soc. 1906, 38, 722; 1908, 40, 790.

RCO2H

1) Br2/P

2) H2OR

Br

CO2H

Ber. Deut. chem. Ges. 1887, 20, 2026.

Lev Aleksandrovich Chugaev(1873-1922)

M. Chem. Moscow 1903Dr. 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)

R2) MeI3) ∆

1) NaOH/CS2ROH

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

Development of α-dioximes as reagents for Group VIIIBmetals (e.g. dimethylglyoxime for nickel)

Z. anorg. allgem. Chem. 1905, 46, 144.

Nikolai Aleksandrovich Menshutkin(1842-1907)

kandidat St. Petersburg 1862M. Chem. St. Petersburg 1866Dr. 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:

NR3

R1R2 N R4

R3

R1R2 XR X+

Z. Phys. Chem. 1890, 5, 589; 1891, 6, 41.

Aleksandr Porfir’evich Borodin(1834-1887)

kandidat St. Petersburg Medical-Surgical Academy 1855M.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)

R BrBr2R CO2Ag

Z. Chem. 1861, 4, 5; 1869, 12, 342.Ann. Chem. Pharm. 1861, 119, 121.

R CHO NaOHCHO

OH

R

R

Ber. Deut. chem. Ges. 1873, 6, 982.

COClKHF2 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 1883M. Chem. St. Petersburg 1891Dr. Chem. St. Petersburg 1895

St. Petersburg Technical Institute• Professor of Chemistry 1896-1907USSR Academy of Sciences• Associate Member 1921• Academician 1929

A. E. Favorskii (Favorsky)(1860-1945)

RCH2 C C H C CR

CH

H

H

CCR CH3

J. Russ. Phys. Chem. Soc. 1887, 19, 414.Ber. Deut. chem. Ges. 1887, 20, 781.

R C C H + OR

RR C C

R

ROH

J. Russ Phys. Chem. Soc. 1900, 32, 652; 1905, 37, 643.Chem. Zentr. 1905, II, 1018.

O

Br

NaOHCO2H

J. prakt. Chem. 1913, 88, 658.

Vyacheslav Evgenievich Tishchenko(1861-1941)

Ar CHOAl(OEt)3

Ar O

O

Ar

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)

R R

O

acid

O

R R

OH

R R

Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1942, 200.

Sergei Semenovich Nametkin(1876-1950)

R R

H

Liebigs Ann. Chem. 1923, 432, 207.