Addition Reactions to Multiple C-Heteroatom Bonds

The addition reactions to multiple C-heteroatom bonds occur when a functional group is added to a carbon-oxygen double bond (C=O) or carbon-nitrogen double bond (C=N), forming a single bond.

This section lists the most significant named organic reactions classified according to the type of chemical reaction. Among the named organic reactions of the addition type to multiple C-heteroatom bonds we can highlight the following:

Barbier reaction

References:
P. Barbier, Compt. Rend. Acad. Sci. Paris 128, 110 (1899)

Baylis-Hillman reaction

References:
A.B. Baylis, M.E.D. Hillman, Ger. Patent 2155113 (1972)

Benzoin condensation

References:
A.J. Lapworth, J. Chem. Soc. 83, 995 (1903)
A.J. Lapworth, J. Chem. Soc. 85, 1206 (1904)

Blaise reaction

References:
E.E. Blaise, M. Maire, Compt. Rend. Acad. Sci. Paris 145, 73 (1907)

Blaise ketone synthesis

References:
E.E. Blaise, A. Koehler, Bull. Soc. Chem. 7, 215 (1910)

Bouveault aldehyde synthesis

References:
L. Bouveault, Bull. Soc. Chim. France, 31, 1306, 1322 (1904)

Claisen condensation

References:
L. Claisen, O. Lowman, Chem. Ber, 20, 651 (1887)

Claisen-Schmidt condensation

Darzens condensation (Darzens-Claisen reaction)

References:
G. Darzens, Compt. Rend. Acad. Sci. Paris 139, 1214 (1904);
G. Darzens, Chem. Zentr. I, 346 (1905)
G. Darzens, Compt. Rend. Acad. Sci. Paris 141, 766 (1905)
G. Darzens, Chem. Zentr. I, 22 (1906)
G. Darzens, Compt. Rend. Acad. Sci. Paris 142, 214 (1906)
G. Darzens, Chem. Zentr. I, 669 (1906)

Doebner reaction

References:
O. Doebner, Ann. 242, 265 (1887)
O. Doebner, Chem. Ber. 20, 277 (1887)
O. Doebner, Chem. Ber. 27, 352 (1894)
O. Doebner, Chem. Ber. 27, 2020 (1894)

Eschweiler-Clarke reaction (Eschweiler–Clarke methylation)

References:
W. Eschweiler, Chem. Ber. 38, 880 (1905)
H.T. Clarke, H.B. Gillespie, S.Z. Weisshaus, J. Am. Chem. Soc. 55, 4571 (1933)

Grignard reaction

References:
V. Grignard, Compt. Rend. Acad. Sci. Paris 130, 1322 (1900)
D.A. Shirley, Org. React. 8, 28-58 (1954)

Kiliani-Fischer synthesis

References:
H. Kiliani, Chem. Ber. 18, 3066 (1885)
H. Kiliani, Chem. Ber. 19, 221 (1886)
H. Kiliani, Chem. Ber. 19, 772 (1886)
H. Kiliani, Chem. Ber. 19, 767 (1886)
H. Kiliani, Chem. Ber. 19, 1128 (1886)
H. Kiliani, Chem. Ber. 19, 3029 (1886)
H. Kiliani, Chem. Ber. 20, 282 (1887)
H. Kiliani, Chem. Ber. 20, 339 (1887)
H. Kiliani, Chem. Ber. 21, 915 (1888)
H. Kiliani, Chem. Ber. 22, 521 (1889)
E. Fischer, Chem. Ber. 22, 2204 (1889)

Knoevenagel condensation

References:
E. Knoevenagel, Chem. Ber. 31, 2596 (1898)
O. Doebner, Chem. Ber. 33, 2140 (1900)

Leuckart-Wallach reaction

References:
R. Leuckart, Chem. Ber. 18, 2341 (1885)
O. Wallach, Justus Liebigs. Ann. Chem. 272, 100 (1892)

Mannich reacction

References:
C. Mannich, W. Krösche, Arch. Pharm. 250, 647 (1912)

Meerwein-Ponndorf-Verley reduction

References:
H. Meerwein and R. Schmidt, Justus Liebigs. Ann. Chem. 444, 221 (1925)
W. Ponndorf, Angew. Chem. 39, 138 (1926)
A. Verley, Bull. Soc. Chim. France 37, 537, 871 (1925)

Michaelis-Arbuzov reaction

References:
A. Michaelis, R. Kaehne, Chem. Ber. 31, 1048 (1898)
A.E. Arbuzov, J. Russ. Phys. Chem. Soc. 38, 687 (1906);
A.E. Arbuzov, Chem. Zentr. II, 1639 (1906)
A.E. Arbuzov, N.P. Kushkova, Zh. Ohah. Khim. S.S.S.R. 6, 283 (1936)

Mukaiyama-Michael reaction

References:
K. Narasaka, K. Soai, Y. Aikawa, T. Mukaiyama, Bull. Chem. Soc. Japan 49, 779 (1976)
T. Mukaiyama, S. Kobayashi, Heterocycles 25, 245 (1987)

Passerini reaction

References:
M. Passerini, Gazz. Chim. Ital. 51, 126 (1921)
M. Passerini, Gazz. Chim. Ital. 51, 181 (1921)
M. Passerini, Gazz. Chim. Ital. 53, 410 (1923)
M. Passerini, Gazz. Chim. Ital. 54, 529 (1924)

Perkin reaction

References:
W.H. Perkin, J. Chem. Soc. 21, 53 (1868)
W.H. Perkin, J. Chem. Soc. 21, 18l (1868)
W.H. Perkin, J. Chem. Soc. 31, 388 (1877)

Peterson olefination

References:
D.J. Peterson, J. Org. Chem. 33, 780 (1968)

Pinner reaction (ortho-ester)

References:
A. Pinner, Chem. Ber. 16, 352 (1883)
A. Pinner, Chem. Ber. 16, 1643 (1883)

Prins reaction

References:
H.J. Prins, Chem. Weekblad, 16, 64 (1919)
H.J. Prins, Chem. Weekblad, 16, 1072 (1919)
H.J. Prins, Chem. Weekblad, 16, 1510 (1919)

Reformatsky reaction

References:
S. Reformatskii, Chem. Ber. 20, 1210 (1887)
S. Reformatskii, J. Russ. Phys. Chem. Soc. 22, 44 (1890)

Ritter reaction

References:
J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc. 70, 4045 (1948)
J.J. Ritter, J. Kalish, J. Am. Chem. Soc. 70, 4048 (1948)
F.R. Benson, J.J. Ritter, J. Am. Chem. Soc. 71, 4128 (1949)
L.W. Hartzel, J.J. Ritter, J. Am. Chem. Soc. 71, 4130 (1949)
R.M. Lusskin, J.J. Ritter, J. Am. Chem. Soc. 72, 5577 (1950)
H. Plaut, J.J. Ritter, J. Am. Chem. Soc. 73, 4076 (1951)

Robinson annulation

 

Schiff reaction (Schiff base)

References:
H. Schiff, Justus Liebigs. Ann. Chem. (Suppl.) 3, 343 (1864-1865)
H. Schiff, Justus Liebigs. Ann. Chem. 140, 93 (1867)
H. Schiff, Justus Liebigs. Ann. Chem. 148, 330 (1868)
H. Schiff, Justus Liebigs. Ann. Chem. 201, 355 (1880)
H. Schiff, Justus Liebigs. Ann. Chem. 210, 114 (1881)
H. Schiff, Chem. Ber. 25, 1936 (1892)

Sonn-Müller method

References:
A. Sonn, E. Müller, Chem. Ber. 52, 1927 (1919)
T. Reichstein, H. Zschokke, Helv. Chim. Acta 15, 1105 (1932)
W.E. Bachmann, J. Am. Chem. Soc. 57, 1381 (1935)

Stephen aldehyde synthesis

References:
H. Stephen, J. Chem, Soc. 127, 1874 (1925)

Stobbe condensation

References:
H. Stobbe, Chem. Ber. 26, 2312 (1893)
H. Stobbe, Justus Liebigs. Ann. Chem. 282, 280 (1894)

Tebbe olefination

References:
F. N. Tebbe, G.W. Parshall, G.S. Reddy, J. Am. Chem. Soc. 100, 3611 (1978)

Thorpe reaction

References:
H. Baron, F. G. P. Remfry, J. F. Thorpe, J. Chem. Soc. 85, 1726 (1904)
J.F. Thorpe et al., J. Chem. Soc. 87, 15 (1905)
J.F. Thorpe et al., J. Chem. Soc. 89, 631 (1906)
J.F. Thorpe et al., J. Chem. Soc. 89, 1906 (1906)
J.F. Thorpe et al., J. Chem. Soc. 91, 578 (1907)
J.F. Thorpe et al., J. Chem. Soc. 91, 1004 (1907)
J.F. Thorpe et al., J. Chem. Soc. 91, 1282 (1907)
J.F. Thorpe et al., J. Chem. Soc. 91, 1687 (1907)
J.F. Thorpe et al., J. Chem. Soc. 93, 165 (1908)
J.F. Thorpe et al., J. Chem. Soc. 99, 422 (1911)
J.F. Thorpe et al., J. Chem. Soc. 103, 1586 (1913)
J.F. Thorpe et al., J. Chem. Soc. 115, 686 (1919)
J.F. Thorpe et al., J. Chem. Soc. 117, 1465 (1920)

Ugi reaction (four-component condensation)

References:
I. Ugi, Angew. Chem. Int. Ed. 1, 8 (1962)

Wittig reaction

References:
G. Wittig, U. Schollkopf, Chem. Ber. 87, 1318 (1954)
G. Wittig, W. Haag, Chem. Ber. 88, 1654 (1955)

Wöhler synthesis

References:
F. Wohler, Pogg. Anal. 12, 253 (1828)

Back to the Named Organic Reactions and Chemical Reagents page.