Elimination reactions

The elimination reaction occurs when two substituents leave the molecule to form an unsaturation, which can be a double bond, triple bond or ring. They occur through two types of unimolecular (E1) and bimolecular (E2) mechanisms.

A particular case of elimination reaction is when the two groups that are detached from the molecule belong to the same carbon, since it results in a carbene (:CR₂).

In this section, the most significant named organic reactions are listed, classified according to the type of chemical reaction. Among the named organic reactions of the elimination type we can highlight the following:

Bamford-Stevens reaction

References:
W. R. Bamford and T. S. Stevens, J. Chem. Soc. 1952, 4735

Boord olefin synthesis

References:
L. C. Swallen and C. E. Boord, J. Am. Chem. Soc. 52, 651 (1930); 53, 1505 (1931); 55, 3293(1933)

Chugaev elimination

References:
L. Chugaev (Tschugaeff), Ber. 32, 3332 (1899)
F. C. Whitman and C. T. Simpson, J. Am. Chem. Soc. 55, 3809 (1933)
P. G. Stevens and J. H. Richmond, J. Am. Chem. Soc. 63, 3132 (1941)
C. H. Depuy, R. W. King, Chem. Rev. 60, 444 (1960)
H. R. Nace, Org. React. 12, 57 (1962)

Cope elimination

References:
A. C. Cope, T. T. Foster and P. H. Towle, J. Am. Chem. Soc. 71, 3929 (1949)
J. Am. Chem. Soc. 75, 3212 (1953)

Corey-Winter Olefin Synthesis

References:
E. J. Corey, R. A. E. Winter, J. Am. Chem. Soc. 85, 2677 (1963)
M. Tichy, J. Sicher, Tetrahedron Letters 1969, 4609

Eschenmoser fragmentation

References:
A. Eschenmoser et al., Helv. Chem. Acta 50,708 (1967)
J. Schreiber et al., ibid. 2101
M. Tanabe et al. Tetrahedron Letters 1967, 3943
D. Felix et al., Helv. Chim. Actga 54 2896-2912 (1971)

Henry reaction (nitroaldol reaction)

References:
L. Henry, Compt. Rend. 120, 1265 (1895)
J. Kamlet, U.S. pat. 2, 151, 517 (1939); C.A. 33, 5003 (1939)
H. B. Hass and E. F. Riley, Chem. Revs. 32 406 (1943)

Hofmann elimination (exhaustive Hofmann methylation)

References:
A. W. Hofmann, Ber. 14, 659 (1881)
H. Gilman, Organic Chemistry ll (Ner York, 1943), p 1172
M. Pailer and L. Bilek, Monatsh. 79, 135 (1948)

Kuhn-Winterstein reaction

References:
R. Kuhn and A. Winterstein, Helv. Chim. Acta 11, 87 (1928)
Kuhn et al., Ber. 71, 1510 (1938); 84, 566 (1938); 84, 566 (1961); 88, 309 (1955)

Ramberg-Bäcklund reaction

References:
L. Ramberg and B. Bäcklund, Arkiv. Kemi Mineral Geol. 13A (27), 50 (1940); C.A. 34, 4725 (1940)

Retro-Diels–Alder reaction

References:
K. Kwart, K. King, Chem. Rev. 68, 415-447 (1968)
O. Papies, W. Grimm, Teterahedron Letters 21, 2799 (1980)

Von Braun amide degradation

References:

H. von Pechmann, Ber. 33, 611 (1900)
J. von Braun, Ber. 37, 3210 (1904)

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