Chapter 12 — Further Reading

Annotated bibliography for elimination reactions.

Textbook treatments

• Clayden, Greeves, Warren (2012). Organic Chemistry, 2nd edition. Oxford. Chapter 19 covers eliminations in depth, with elegant treatment of E1cb and the spectrum of mechanisms between E2 and E1.

• Carey, F. A., and Sundberg, R. J. (2007). Advanced Organic Chemistry, Part A, 5th edition. Springer. Chapter 5 includes elimination mechanisms.

• Saunders, W. H. (1972). Mechanisms of Elimination Reactions. Wiley-Interscience. The classical monograph; still cited.

• Anslyn, E. V., and Dougherty, D. A. (2006). Modern Physical Organic Chemistry. University Science Books. Chapter 10 (More O'Ferrall–Jencks plots) addresses the SN/E continuum rigorously.

Foundational mechanism work

• Hughes, E. D., and Ingold, C. K. (1933). The mechanisms of elimination reactions. Series of papers in J. Chem. Soc. The original $E1$/$E2$ distinction.

• Bunnett, J. F. (1969). The variable transition state in elimination reactions. Acc. Chem. Res. 2, 23. On the spectrum of mechanisms from "pure E1" to "pure E2."

• More O'Ferrall, R. A. (1970). Relationship between E2 and E1cb mechanisms. J. Chem. Soc. B 274. The classical paper introducing energy-surface analysis of elimination mechanisms.

On Hofmann elimination

• Hofmann, A. W. (1851). Annalen der Chemie. The original report. (German.)

• Cope, A. C., and Trumbull, E. R. (1960). The Cope rearrangement and Cope elimination. Org. React. 11, 317.

• Banthorpe, D. V. (1963). Elimination Reactions. Elsevier. Includes a chapter on Hofmann variants.

On cyclohexane stereochemistry in E2

• Saunders, W. H., and Cockerill, A. F. (1973). Mechanisms of Elimination Reactions. Wiley. The chapter on conformational requirements for E2 in cyclic systems.

• Bartlett, P. D., et al. Several papers on the stereochemistry of E2 in cyclohexanes; cited in standard textbooks.

On industrial alkene production

• Matar, S., and Hatch, L. F. (2001). Chemistry of Petrochemical Processes, 2nd edition. Butterworth-Heinemann.

• Plotkin, J. S. (2017). The propylene supply problem. Chem. Eng. News. On industrial-scale alkene production.

On enzymatic eliminations (E1cb in biology)

• Frey, P. A., and Hegeman, A. D. (2007). Enzymatic Reaction Mechanisms. Oxford University Press. Chapter on dehydratases and lyases — biological E1cb mechanisms.

• Walsh, C. T. (1979). Enzymatic Reaction Mechanisms. Freeman. Older but foundational.

On the SN/E competition (preview of Ch 13)

• Reichardt, C., and Welton, T. (2010). Solvents and Solvent Effects in Organic Chemistry, 4th edition. Wiley-VCH. Chapter on SN/E competition.

• Klein, D. Organic Chemistry as a Second Language. The companion workbook on SN/E decision-making is highly recommended for students who struggle with the framework.