II: Radical Reactions of Carbohydrates
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Whenever a structural change is needed in a molecule, an early (if not the first) question is “What is the best way to accomplish this change?” For many years the answer to this question rarely involved a radical reaction (unless polymerization was taking place) because the synthetic potential of radical reactions was viewed in a negative light.1 As understanding of radical reactions blossomed during the latter part of the 20th Century, this situation changed, and radical-based processes were seen increasingly not only as synthetically viable possibilities but often as the best choice. Nowhere was the option of conducting a radical reaction more attractive than in carbohydrate chemistry because the combined chemoselectivity, regioselectivity, and stereoselectivity of these reactions was particularly well suited for structural change in polyfunctional molecules.
1: Advantages & Disadvantages of Radical Reactions
2: Halogenated Compounds
3: Compounds with Carbon–Sulfur Single Bonds
4: Selenides & Tellurides
5: Acetals & Ethers
6: Alkoxy Radicals
7: Unprotected Carbohydrates
8: Carboxylic Acids & Esters
9: Phosphoric Acid Esters
10: Aldehydes & Ketones
11: Synthesis of O-Thiocarbonyl Compounds
12: Reactions of O-Thiocarbonyl Compounds
13: Carboxylic Acid Esters of N-Hydroxypyridine-2-thione
14: Nitro Compounds
15: Azides & Azo Compounds
16: Nitriles & Isonitriles
17: Oxime Ethers & Related Compounds
18: Compounds with Carbon–Carbon Multiple Bonds I: Addition Reactions
19: Compounds With Carbon–Carbon Multiple Bonds II: Cyclization Reactions
20: Reactions of Samarium(II) Iodide With Carbohydrate Derivatives
21: Reactions of Radicals Produced by Electron Transfer to Manganese(III) Acetate & Ammonium Cerium(IV) Nitrate
22: Reactions of Carbohydrate Derivatives With Titanocene(III) Chloride
23: Organocobalt & Organomercury Compounds
24: Redox Couples
Appendix I: Hydrogen-Atom Donors
References
Contributors
Roger W. Binkley (Cleveland State University) and Edith R. Binkley (Cleveland Heights-University Heights school system)