Radical Reactions of Carbohydrates II: Radical Reactions of Carbohydrates
- Page ID
- 23799
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)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.
- Front Matter
- 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
- Back Matter