Abstract
Addition and elimination processes are the reverse of one another. In general, the two processes follow a similar mechanistic path in opposite directions, the final state of the system depending on the conditions. For example, hydration of alkenes and dehydration of alcohols are both familiar reactions that constitute a related addition— elimination pair.
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General References
Polar Addition Reactions
P. B. D. de la Mare and R. Bolton, Electrophilic Additions to Unsaturated Systems, Second Edition, Elsevier, New York, 1982.
R. C. Fahey, in Topics in Stereochemistry, Vol. 3, E. L. Eliel and N. L. Allinger (eds.), Interscience, New York, 1968, pp. 237–342.
G. H. Schmid and D. G. Garrat, in The Chemistry of Double-Bonded Functional Groups, Part 2, Wiley, New York, 1977, Chap. 9.
G. H. Schmid, in The Chemistry of the Carbon—Carbon Triple Bond, Part 1, S. Patai (ed.), Wiley, New York, 1978, Chap. 8.
Elimination Reactions
W. H. Saunders, Jr., and A. F. Cockerill, Mechanisms of Elimination Reactions, Wiley, New York, 1973.
N. A. LeBel, Adv. Alicyclic Chem. 3, 195 (1971).
J. F. Bunnett, Surv. Prog. Chem. 5, 53 (1969).
A. F. Cockerill and R. G. Harrison, The Chemistry of Double-Bonded Functional Groups, Part 1, S. Patai (ed.), Wiley, New York, 1977, Chap. 4.
Chapter 6
K. Yates, G. H. Schmid, T. W. Regulski, D. G. Garratt, H.-W. Leung, and R. McDonald, J. Am. Chem. Soc. 95, 160 (1973).
J. F. King and M. J. Coppen, Can. J. Chem. 49, 3714 (1971).
N. C. Deno, F. A. Kish, and H. J. Peterson, J. Am. Chem. Soc. 87, 2157 (1965).
M. A. Cooper, C. M. Holden, P. Loftus, and D. Whittaker, J. Chem. Soc. Perkin Trans. II, 665 (1973).
R. A. Bartsch and J. F. Bunnett, J. Am. Chem. Soc. 91, 1376 (1969).
K. Yates and T. A. Go, J. Org. Chem. 45, 2377 (1980).
C. B. Quinn and J. R. Wiseman, J. Am. Chem. Soc. 95, 1342 (1973).
H. Wong, J. Chapuis, and I. Monković, J. Org. Chem. 39, 1042 (1974).
P. K. Freeman, F. A. Raymond, and M. F. Grostic, J. Org. Chem. 32, 24 (1967).
T. I. Crowell, R. T. Kemp, R. E. Lutz, and A. A. Wall, J. Amn. Chem. Soc. 90, 4638 (1968).
L. C. King, L. A. Subluskey, and E. W. Stern, J. Org. Chem. 21, 1232 (1956).
M. L. Poutsma and P. A. Ibarbia, J. Am. Chem. Soc. 93, 440 (1971).
S. P. Acharya and H. C. Brown, Chem. Commun. 305 (1968).
A. Lewis and J. Azoro, J. Org. Chem. 46, 1764 (1981).
K. Yates and T. A. Go, J. Org. Chem. 45, 2377 (1980).
D. Y. Curtin, R. D. Stolow, and W. Maya, J. Am. Chem. Soc. 81, 3330 (1959).
W. H. Saunders and A. F. Cockerill, Mechanisms of Elimination Reactions, Wiley, New York, 1973, pp. 79, 80.
M. Anteunis and H. L. Peeters. J. Org. Chem. 40, 307 (1975).
D. S. Noyce, D. R. Hartter, and R. M. Pollack, J. Am. Chem. Soc. 90, 3791 (1968).
C. L. Wilkins and T. W. Regulski, J. Am. Chem. Soc. 94, 6016 (1972).
R. A. Bartsch, J. Am. Chem. Soc. 93, 3683 (1971).
K. Oyama and T. T. Tidwell, J. Am. Chem. Soc. 98, 947 (1976).
K. D. Berlin, R. O. Lyerla, D. E. Gibbs, and J. P. Devlin, Chem. Commun. 1246 (1970).
R. J. Abraham and J. R. Monasterios, J. Chem. Soc. Perkin Trans. II, 574 (1975).
H. C. Brown and K.-T. Liu, J. Am. Chem. Soc. 97, 2469 (1975).
D. J. Pasto and J. A. Gontarz, J. Am. Chem. Soc. 93, 6902 (1971).
J. F. Bunnett and S. Sridharan, J. Org. Chem. 44, 1458 (1979);
L. F. Blackwell, A. Fischer, and J. Vaughan, J. Chem. Soc., B, 1084 (1967).
J. E. Nordlander, P. O. Owuor, and J. E. Haky, J. Am. Chem. Soc. 101, 1288 (1979).
G. E. Heasley, T. R. Bower, K. W. Dougharty, J. C. Easdon, V. L. Heasley, S. Arnold, T. L. Carter, D. B. Yaeger, B. T. Gipe, and D. F. Shellhamer, J. Org. Chem. 45, 5150 (1980).
P. Cramer and T. T. Tidwell, J. Org. Chem. 46, 2683 (1981).
R. C. Fahey and C. A. McPherson, J. Am. Chem. Soc. 91, 3865 (1965);
R. C. Fahey, M. W. Monahan, and C. A. McPherson, J. Am. Chem. Soc. 92, 2810 (1970).
C. H. DePuy and A. L. Schultz, J. Org. Chem. 39, 878 (1974).
T. T. Coburn and W. M. Jones, J. Am. Chem. Soc. 96, 5218 (1974).
R. B. Miller and G. McGarvey, J. Org. Chem. 44, 4623 (1979).
P. F. Hudrlik and D. Peterson, J. Am. Chem. Soc. 97, 1464 (1975).
G. Bellucci, A. Marsili, E. Mastrorilli, I. Morelli, and V. Scartoni, J. Chem. Soc. Perkin Trans. II, 201 (1974).
D. S. Noyce, D. R. Hartter, and F. B. Miles, J. Am. Chem. Soc. 90, 3794 (1968).
Y. Pocker, K. D. Stevens, and J. J. Champoux, J. Am. Chem. Soc. 91, 4199 (1969).
M. F. Ruasse, A. Argile, and J. E. Dubois, J. Am. Chem. Soc. 100, 7645 (1978).
W. K. Chwang, P. Knittel, K. M. Koshy, and T. T. Tidwell, J. Am. Chem. Soc. 99, 3395 (1977).
D. J. Pasto and J. F. Gadberry, J. Am. Chem. Soc. 100, 1469 (1978).
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Carey, F.A., Sundberg, R.J. (1984). Polar Addition and Elimination Reactions. In: Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-1143-1_6
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DOI: https://doi.org/10.1007/978-1-4757-1143-1_6
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