Chapter 36 — Further Reading

Textbooks

• Hudlicky, M. (1990). Oxidations in Organic Chemistry. American Chemical Society. The classic reference for oxidation methods.

• Hudlicky, M. (1984). Reductions in Organic Chemistry. Ellis Horwood. The companion volume on reductions.

• March's Advanced Organic Chemistry, 7th ed. (Wiley, 2013). Chapters on oxidations and reductions.

• Carey and Sundberg. Advanced Organic Chemistry, Part B: Reactions and Synthesis, 5th ed. (Springer, 2007). Chapters 11 and 12 cover oxidation/reduction.

• Larock, R. C. (1989). Comprehensive Organic Transformations. VCH. Encyclopedic; thousands of methods including all common oxidations and reductions.

Primary literature: oxidation methods

• Corey, E. J., and Suggs, J. W. (1975). PCC for alcohol oxidation. Tetrahedron Letters 16(31), 2647-2650. The PCC method.

• Dess, D. B., and Martin, J. C. (1983). The DMP method. Journal of Organic Chemistry 48, 4155-4156. The introduction of Dess-Martin periodinane.

• Mancuso, A. J., and Swern, D. (1981). The Swern oxidation. Synthesis. The DMSO/oxalyl chloride method.

• Sharpless, K. B., Akashi, K., and Oshima, K. (1976). The original Sharpless dihydroxylation. Tetrahedron Letters.

• Sharpless, K. B. (1988). The asymmetric dihydroxylation with chiral cinchona ligands. Journal of the American Chemical Society 110, 1968-1970.

• Sharpless, K. B. (2002). Nobel Lecture. Angewandte Chemie 41(12), 2024-2032. Sharpless's narrative of the AE/AD discoveries.

Primary literature: reduction methods

• Brown, H. C., and Subba Rao, B. C. (1956). NaBH₄ for ketone reductions. Journal of the American Chemical Society 78, 2582. Brown Nobel 1979.

• Finholt, A. E., et al. (1947). LiAlH₄ as universal reducing agent. Journal of the American Chemical Society 69, 1199.

• Corey, E. J., Bakshi, R. K., and Shibata, S. (1987). The CBS reagent for asymmetric reduction. Journal of the American Chemical Society 109, 5551-5553.

• Noyori, R. (2002). Nobel Lecture. Angewandte Chemie 41(12). Noyori's asymmetric hydrogenation work.

• Knowles, W. S. (2002). Nobel Lecture. Angewandte Chemie 41(12). Knowles's L-DOPA synthesis via asymmetric hydrogenation.

Asymmetric catalysis

• Sharpless, K. B., et al. (multiple papers, 1980-1990). The asymmetric oxidations.

• Noyori, R., et al. (multiple papers). Ru/BINAP and other asymmetric hydrogenations.

• Jacobsen, E. N., et al. (1990). Mn-salen catalysts for asymmetric epoxidation. Journal of the American Chemical Society 112, 2801-2803.

• Shi, Y., et al. (1996). Chiral fructose-derived ketone for asymmetric epoxidation. Journal of the American Chemical Society 118, 9806-9807.

Biological redox

• Walsh, C. T. (1979). Enzymatic Reaction Mechanisms. W. H. Freeman. Comprehensive treatment of enzyme redox chemistry.

• Bissett, T. R., and Stojanoff, V. (2018). Crystal structures of NAD-dependent enzymes. Various papers.

• Sjöström, P. E., et al. (2018). NAD homeostasis and aging. Cell Metabolism 28(2), 188-194.

• Bonkowski, M. S., and Sinclair, D. A. (2016). Slowing aging via increased NAD. Nature Reviews Molecular Cell Biology 17, 679-690.

Drug metabolism (CYP enzymes)

• Guengerich, F. P. (2008). "Cytochrome P450 enzymes." Chemical Research in Toxicology 21(1), 70-83. Comprehensive review.

• Wienkers, L. C., and Heath, T. G. (2005). Drug-drug interactions via CYP3A4. Drug Metabolism Reviews 37(3), 469-489.

Industrial applications

• Mark, R. J., et al. (2003). Industrial Sharpless AD: scale-up to ton scale. Organic Process Research & Development 7(6), 1102-1106.

• Caron, S., et al. (eds.) (2011). Practical Synthetic Organic Chemistry. Wiley. Industrial perspective on oxidation and reduction.

Computational tools

• Avogadro (https://avogadro.cc/). Visualize transition states for oxidation/reduction.

• PubChem — look up: PCC (CID 65067), DMP (CID 11013870), NaBH₄ (CID 4311764), LiAlH₄ (CID 28112), NAD (CID 5893), NADH (CID 5892).

Online resources

• Master Organic Chemistry, "Oxidation and Reduction" series. Free, undergraduate-level.

• Khan Academy: Organic Chemistry — Oxidation and Reduction. Free videos.

• Reaxys for searching specific oxidation reactions.

For practice problems

• Klein, David. Organic Chemistry as a Second Language, 4th ed. (Wiley). Chapter on oxidation and reduction.

• Karty, Joel. Organic Chemistry: Principles and Mechanisms, 2nd ed. (W. W. Norton, 2018). Chapter on redox chemistry.

Notes on this chapter's pedagogy

Chapter 36 takes the unifying view that all redox chemistry is about counting oxidation states. By treating PCC, Jones, NaBH₄, LiAlH₄, etc. as different chemoselective reagents that achieve the same kinds of transformations, we help students see the connections.

The chapter ends with biological redox (NAD, FAD, CYP) and asymmetric catalysis (Sharpless), connecting the basic chemistry to its modern applications. Chapter 37 continues with organometallic chemistry, including the asymmetric catalysts mentioned here.