Zusammenfassung
Wir alle haben am Beginn des Chemiestudiums gelernt, Oxidationszahlen in anorganischen Verbindungen zu bestimmen.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Literatur
S. D. Burke, R. L. Danheiser (Hrsg.), „Handbook of Reagents for Organic Synthesis: Oxidizing and Reducing Agents“, Wiley, New York, 1999.
17.1
G. Calzaferri, „Oxidation Numbers“, J. Chem. Ed. 1999, 76, 362–363.
17.3
A. H. Haines, „Methods for the Oxidation of Organic Compounds: Alkanes, Alkenes, Alkynes, Arenes“, AP, New York, 1985.
A. H. Haines, „Methods for the Oxidation of Organic Compounds: Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes, and Aminoarenes“, Academic Press, 1988.
M. Hudlicky, „Oxidations in Organic Chemistry“, American Chemical Society, Washington, DC, 1990.
H. Bornowski, D. Döpp, R. Jira, U. Langer, H. Offermans, K. Praefcke, G. Prescher, G. Simchen, D. Schumann, „Preparation of Aldehydes by Oxidation“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Aldehydes (J. Falbe, Hrsg.), Bd. E3, 231, Georg Thieme Verlag, Stuttgart, 1983.
A. J. Mancuso, D. Swern, „Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis“, Synthesis 1981, 165.
T. T. Tidwell, „Oxidation of alcohols by activated dimethyl sulfoxide and related reactions: an update“, Synthesis 1990, 857–870.
T. T. Tidwell, „Oxidation of Alcohols to Carbonyl Compounds via Alkoxysulfonium Ylides: The Moffatt, Swern, and Related Oxidations“, Org. React. 1990, 39, 297–572.
F. A. Luzzio, „The Oxidation of Alcohols by Modified Oxochromium(VI)-Amine Reagents“, Org. React. 1998, 53, 1–221.
E. J. de Nooy, A. C. Besemer, H. van Bekkum, „On the Use of Stable Organic Nitroxyl Radicals for the Oxidation of Primary and Secondary Alcohols“, Synthesis, 1996, 1153–1174.
R. M. Moriarty, O. Prakash, „Oxidation of Carbonyl Compounds with Organohypervalent Iodine Reagents“, Org. React. 1999, 54, 273–418.
J. B. Arterburn, „Selective Oxidation of Secondary Alcohols“, Tetrahedron 2001, 57, 9765–9788.
D. V. Deubel, G. Frenking, „[3 + 2] Versus [2 + 2] Addition of Metal Oxides Across C=C Bonds. Reconciliation of Experiment and Theory“, Acc. Chem. Res. 2003, 36, 645–651.
R. A. Johnson, K. B. Sharpless, „Catalytic Asymmetric Dihydroxylation-Discovery and Development“, in Catalytic Asymmetric Synthesis (I. Ojima, Hrsg.), Wiley-VCH, New York, 2. Aufl., 2000, 357–389.
C. Bolm, J. P. Hildebrand, K. Muniz, „Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation“, in Catalytic Asymmetric Synthesis, (I. Ojima, Hrsg.), Wiley-VCH, New York, 2. Aufl., 2000, 399–428.
D. Nilov, O. Reiser, „The Sharpless Asymmetric Aminohydroxylation - Scope and Limitation“, Adv. Synth. Catal. 2002, 344, 1169–1173.
J. A. Bodkin, M. D. McLeod, „The Sharpless Asymmetric Aminohydroxylation“, J. Chem. Soc. Perkin Trans. I 2002, 2733–2746.
R. L. Kuczkowski, „The structure and mechanism of formation of ozonides“, Chem. Soc. Rev. 1992, 21, 79–83.
E. L. Jackson, „Periodic Acid Oxidation“, Org. React. 1944, 2, 341–375.
C. H. Hassall, „The Baeyer-Villiger Oxidation of Aldehydes and Ketones“, Org. React. 1957, 9, 73–106.
G. R. Krow, „The Baeyer-Villiger Reaction“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 7, 671, Pergamon Press, Oxford, U. K., 1991.
G. R. Krow, „The Bayer-Villiger Oxidation of Ketones and Aldehydes“, Org. React. 1993, 43, 251–798.
17.4
M. Hudlicky, „Reductions in Organic Chemistry“, The Royal Society of Chemistry, Cambridge, U. K., 1996.
A. F. Abdel-Magid (Hrsg.), „Reductions in Organic Synthesis: Recent Advances and Practical Applications“, ACS Symposium Series, The Royal Society of Chemistry, Cambridge, U. K., 1996.
A. Hajos, „Reduction with Inorganic Reducing Agents – Metal Hydrides and Complex Hydrides“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Reduction Part II (H. Kropf, Hrsg.), Bd. 4/1d, 1, Georg Thieme Verlag, Stuttgart, 1981.
W. G. Brown, „Reductions by Lithium Aluminum Hydride“, Org. React. 1951, 6, 469–509.
J. Malek, „Reductions by Metal Alkoxyaluminum Hydrides“, Org. React. 1985, 34, 1–317.
J. Malek, „Reduction by Metal Alkoxyaluminum Hydrides. Part II. Carboxylic Acids and Derivatives, Nitrogen Compounds, and Sulfur Compounds“, Org. React. 1988, 36, 249–590.
J. Seyden-Penne, „Reductions by the Alumino- and Borohydrides in Organic Synthesis“, VCH, New York, 1991.
A. J. Downs, C. R. Pulham, „The Hydrides Of Aluminum, Gallium, Indium, And Thallium – A Reevaluation“, Chem. Soc. Rev. 1994, 23, 175.
N. M. Yoon, „Selective Reduction of Organic Compounds with Aluminum and Boron Hydrides“, Pure Appl. Chem. 1996, 68, 843.
J. Seyden-Penne, „Reductions by the Alumino- and Borohydrides in Organic Synthesis“, 2. Aufl., Wiley, New York, 1997.
G. W. Gribble, „Sodium Borohydride in Carboxylic Acid Media: A Phenomenal Reduction System“, Chem. Soc. Rev. 1998, 27, 395–404.
L. K. Keefer, G. Lunn, „Nickel-Aluminum Alloy as a Reducing Agent“, Chem. Rev. 1989, 89, 459–502.
T. Imamoto, „Reduction of Saturated Alkyl Halides to Alkanes“, in Comprehensive Or-ganic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 793, Pergamon Press, Oxford, U. K., 1991.
S. W. McCombie, „Reduction of Saturated Alcohols and Amines to Alkanes“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 811, Pergamon Press, Oxford, U. K., 1991.
A. G. Sutherland, „One or More CH Bond(s) Formed by Substitution: Reduction of C-Halogen and C-Chalcogen Bonds“, in Comprehensive Organic Functional Group Transformations (A. R. Katritzky, O. Meth-Cohn, C. W. Rees, Hrsg.), Bd. 1, 1, Elsevier Science, Oxford, U. K., 1995.
W. H. Hartung, R. Simonoff, „Hydrogenolysis of Benzyl Groups Attached to Oxygen, Nitrogen, or Sulfur“, Org. React. 1953, 7, 263–326.
A. Gansäuer, S. Narayan, ”Titanocene-Catalyzed Electron Transfer-Mediated Opening of Epoxides“, Adv. Synth. Catal. 2002, 344, 465–475.
C. Blomberg, „The Barbier Reaction and Related One-Step Processes“, Springer-Verlag, Heidelberg, 1994.
C. G. Screttas, B. R. Steele, „Organometallic Carboxamidation. A Review“, Org. Prep. Proced. Int. 1990, 22, 269–314.
T. Cohen, M. Bhupathy, „Organoalkali Compounds by Radical Anion Induced Reductive Metalation of Phenyl Thioethers“, Acc. Chem. Res. 1989, 22, 152–161.
M. Yus, „Arene-Catalyzed Lithiation Reactions“, Chem. Soc. Rev. 1996, 25, 155–162.
M. Yus, F. Foubelo, „Reductive Opening of Saturated Oxa-, Aza- and Thia-Cycles by Means of an Arene-Promoted Lithiation: Synthetic Applications“, Rev. Heteroatom Chem. 1997, 17, 73–108.
L. Eberson, „Problems and Prospects of the Concerted Dissociative Electron-Transfer Mechanism“, Acta Chem. Scand. 1999, 53, 751–764.
D. J. Ramon, M. Yus, „New Methodologies Based on Arene-Catalyzed Lithiation Reactions and Their Application to Synthetic Organic Chemistry“, Eur. J. Org. Chem. 2000, 225–237.
C. Najera, M. Yus, „Functionalized Organolithium Compounds: New Synthetic Adventures“, Curr. Org. Chem. 2003, 7, 867–926.
Y. H. Lai, „Grignard Reagents from Chemically Activated Magnesium“, Synthesis 1981, 585.
C. Walling, „The Nature of Radicals Involved in Grignard Reagent Formation“, Acc. Chem. Res. 1991, 24, 255.
H. M. Walborsky, „Mechanism of Grignard Reagent Formation. The Surface Nature of the Reaction“, Acc. Chem. Res. 1990, 23, 286–293.
H. M. Walborsky, „Wie entsteht eine Grignard-Verbindung?“, Chem. unserer Zeit, 1991, 25, 108–116.
J. F. Garst, „Grignard Reagent Formation and Freely Diffusing Radical Intermediates“, Acc. Chem. Res. 1991, 24, 95–97.
R. D. Rieke, M. S. Sell, „Magnesium Activation“, in Handbook of Grignard Reagents (G. S. Silverman, P. E. Rakita, Hrsg.), Marcel Dekker Inc., New York, 1996, 53–78.
C. Humdouchi, H. M. Walborsky, „Mechanism of Grignard Reagent Formation“, in Handbook of Grignard Reagents (G. S. Silverman, P. E. Rakita, Hrsg.), Marcel Dekker Inc., New York, 1996, 145–218.
J. F. Garst, F. Unváry, „Mechanisms of Grignard Reagent Formation“, in Grignard Reagents – New Developments, Hrsg.: H. G. Richey, Jr., John Wiley & Sons, Chichester, U. K., 2000, 185–275
R. D. Rieke, „The Preparation of Highly Reactive Metals and the Development of Novel Organometallic Reagents“, Aldrichimica Acta 2000, 33, 52–60.
R. D. Rieke, „Preparation of Organometallic Compounds from Highly Reactive Metal Powders“, Science 1989, 246, 1260–1264.
A. Gansäuer, H. Bluhm, „Reagent-Controlled Transition-Metal-Catalyzed Radical Reactions“, Chem. Rev. 2000, 100, 2771–2788.
J. S. Thayer, „Not for Synthesis Only: The Reactions of Organic Halides with Metal Surfaces“, Adv. Org. Chem. 1995, 38, 59–78.
D. Caine, „Reduction and Related Reactions of a, b-Unsaturated Compounds with Metals in Liquid Ammonia“, Org. React. 1976, 23, 1–258.
J. W. Huffman, „Reduction of CpX to CHXH by Dissolving Metals and Related Methods“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 107, Pergamon Press, Oxford, U. K., 1991.
A. M. El-Khawaga, H. M. R. Hoffmann, „Formation of C-H Bonds by the Reduction of C=C Double Bonds and of Carbonyl Groups with Metals (‘Dissolving Metal Reduction’)“, in Stereoselective Synthesis (Houben-Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 7, 3967–3987, Georg Thieme Verlag, Stuttgart.
S. M. McElvain, „The Acyloins“, Org. React. 1948, 4, 256–268.
J. J. Bloomfield, D. C. Owsley, J. M. Neike, „The Acyloin Condensation“, Org. React. 1976, 23, 259–403.
R. Brettle, „Acyloin Coupling Reactions“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 3, 613, Pergamon Press, Oxford, U. K., 1991.
G. M. Robertson, „Pinacol Coupling Reactions“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 3, 563, Pergamon Press, Oxford, U. K., 1991.
G. C. Fu, „Pinacol Coupling“, in Modern Carbonyl Chemistry (J. Otera, Hrsg.), Wiley-VCH, Weinheim, 2000, 69–91.
O. Hammerich, M. F. Nielsen, „The Competition Between the Dimerization of Radical Anions and Their Reactions with Electrophiles“, Acta Chem. Scand. 1998, 52, 831–857.
D. Lenoir, „The application of low-valent titanium reagents in organic synthesis“, Synthesis 1989, 12, 883–897.
J. E. McMurry, „Carbonyl-Coupling Reactions Using Low-Valent Titanium“, Chem. Rev. 1989, 89, 1513–1524.
T. Lectka, „The McMurry Recation“, in Active Metals (A. Fürstner, Hrsg.), 85, VCH, Weinheim, Germany, 1996.
A. Fürstner, B. Bogdanovic, „Neue Entwicklungen in der Chemie von niedervalentem Titan“, Angew. Chem. 1996, 108, 2582–2609; „New Developments in the Chemistry of Low-Valent Titanium“, Angew. Chem. Int. Ed. Engl. 1996, 35, 2442–2469.
A. G. M. Barrett, „Reduction of Carboxylic Acid Derivatives to Alcohols, Ethers and Amines“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 235, Pergamon Press, Oxford, U. K., 1991.
E. Mosettig, R. Mozingo, „The Rosenmund Reduction of Acid Chlorides to Aldehydes“, Org. React. 1948, 4, 362–377.
E. Mosettig, „The Synthesis of Aldehydes from Carboxylic Acids“, Org. React. 1954, 8, 218–257.
J. S. Cha, „Recent Developments in the Synthesis of Aldehydes by Reduction of Carboxylic Acids and their Derivatives with Metal Hydrides“, Org. Prep. Proced. Int. 1989, 21, 451–477.
A. P. Davis, „Reduction of Carboxylic Acids to Aldehydes by Other Methods“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 283, Pergamon Press, Oxford, U. K., 1991.
N. Greeves, „Reduction of CpO to CHOH by Metal Hydrides“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 1, Pergamon Press, Oxford, U. K., 1991.
H. Brunner, „Formation of C-H Bonds by Reduction of Carbonyl Groups (CpO) – Hydrogenation“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Stereoselective Synthesis (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), Bd. E21d, 3945, Georg Thieme Verlag, Stuttgart, 1995.
A. P. Davis, M. M. Midland, L. A. Morell, „Formation of C-H Bonds by Reduction of Carbonyl Groups (CpO), Reduction of Carbonyl Groups with Metal Hydrides“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Stereoselective Synthesis (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), Bd. E21d, 3988, Georg Thieme Verlag, Stuttgart, 1995.
M. M. Midland, L. A. Morell, K. Krohn, „Formation of C-H Bonds by Reduction of Carbonyl Groups (C=O) – Reduction with C-H Hydride Donors“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Stereoselective Synthesis (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), Bd. E21d, 4082, Georg Thieme Verlag, Stuttgart, 1995.
D. Todd, „The Wolff-Kishner Reduction“, Org. React. 1948, 4, 378–422.
R. O. Hutchins, „Reduction of CpX to CH2 by Wolff-Kishner and Other Hydrazone Methods“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 327, Pergamon Press, Oxford, U. K., 1991.
E. L. Martin, „The Clemmensen Reduction“, Org. React. 1942, 1, 155–209.
H. Meerwein, K. Wunderlich, K. F. Zenner; „Ionische Hydrierungen und Dehydrierungen“, Angew. Chem. 1962, 74, 807–811; „Ionic Hydrogenations and Dehydrogenations“, Angew. Chem. Int. Ed. Engl. 1962, 1, 613–617.
E. Vedejs, „Clemmensen Reduction of Ketones in Anhydrous Organic Solvents“, Org. React. 1975, 22, 401–422.
G. R. Pettit, E. E. van Tamelen, „Desulfurization with Raney Nickel“, Org. React. 1962, 12, 356–529.
P. N. Rylander, „Hydrogenation Methods“, in Best Synthetic Methods, Academic Press, 1985.
H. Brunner, „Hydrogenation with Molecular Hydrogen“, in Stereoselective Synthesis (Houben- Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 7, 3945–3966, Georg Thieme Verlag, Stuttgart.
U. Kazmaier, J. M. Brown, A. Pfaltz, P. K. Matzinger, H. G. W. Leuenberger, „Formation of C–BH Bonds by Reduction of Olefinic Double Bonds – Hydrogenation“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Stereoselective Synthesis (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), Bd. E21d, 4239, Georg Thieme Verlag, Stuttgart, 1995.
V. A. Semikolenov, „Modern approaches to the preparation of, palladium on charcoal‘ catalysts“, Russ. Chem. Rev. 1992, 61, 168–174.
M. D. Navalikhina, O. V. Krylov, „Heterogeneous Hydrogenation Catalysts“, Russ. Chem. Rev. 1998, 67, 587–616.
A. J. Birch, D. H. Williamson, „Homogeneous Hydrogenation Catalysts in Organic Solvents“, Org. React. 1976, 24, 1–186.
H. Takaya, „Homogeneous Catalytic Hydrogenation of C=C and Alkynes“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 443, Pergamon Press, Oxford, U. K., 1991.
R. Noyori, H. Takaya, „BINAP: An Efficient Chiral Element for Asymmetric Catalysis“, Acc. Chem. Res. 1990, 23, 345–350.
R. Noyori, „Binaphthyls as Chiral Elements for Asymmetric Synthesis“, in Stereocontrolled Organic Synthesis (B. M. Trost, Hrsg.), Blackwell Scientific Publications, Oxford, U. K., 1994, 1–15.
T. Ohkuma, M. Kitamura, R. Noyori, „Asymmetric Hydrogenation“, in Catalytic Asymmetric Synthesis (I. Ojima, Hrsg.), Wiley-VCH, New York, 2. Aufl., 2000, 1–110.
V. Ratovelomanana-Vidal, J.-P. Genet, „Synthetic Applications of the Ruthenium-Catalyzed Hydrogenation via Dynamic Kinetic Resolution“, Can. J. Chem. 2000, 78, 846–851.
K. Rossen, „Ru- and Rh-Catalyzed Asymmetric Hydrogenations: Recent Surprises from an Old Reaction“, Angew. Chem. 2001, 113, 4747–4749; Angew. Chem. Int. Ed. Engl. 2001, 40, 4611–4613.
J. M. Hook, L. N. Mander, „Recent Developments in the Birch Reduction of Aromatic Compounds: Applications to the Synthesis of Natural Products“, Nat. Prod. Rep. 1986, 3, 35.
P. W. Rabideau, „The Metal-Ammonia Reduction of Aromatic Compounds“, Tetrahedron 1989, 45, 1579–1603.
L. N. Mander, „Partial Reduction of Aromatic Rings by Dissolving Metals and by Other Methods“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 489, Pergamon Press, Oxford, U. K., 1991.
P. W. Rabideau, Z. Marcinow, „The Birch Reduction of Aromatic Compounds“, Org. React. 1992, 42, 1–334.
A. J. Birch, „The Birch Reduction in Organic Synthesis“, Pure Appl. Chem. 1996, 68, 553–556.
H.-J. Deiseroth, „Alkalimetall-Amalgame“, Chem. unserer Zeit, 1991, 25, 83–86.
Weiterführende Literatur
A. B. Jones, „Oxidation Adjacent to XpX Bonds by Hydroxylation Methods“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 7, 151, Pergamon Press, Oxford, U. K., 1991.
J. Cason, „Synthesis of Benzoquinones by Oxidation“, Org. React. 1948, 4, 305–361.
P. T. Gallagher, „The Synthesis of Quinones“, Contemp. Org. Synth. 1996, 3, 433–446.
V. D. Filimonov, M. S. Yusubov, Ki-WhanChi, „Oxidative Methods in the Synthesis of Vicinal Di- and Poly-Carbonyl Compounds“, Russ. Chem. Rev. 1998, 67, 803–826.
S. Akai, Y. Kita, „Recent Progress in the Synthesis of p-Quinones and p-Dihydroquinones Through Oxidation of Phenol Derivatives“, Org. Prep. Proced. Int. 1998, 30, 603–629.
J. Tsuji, „Synthetic Applications of the Palladium-Catalysed Oxidation of Olefins to Ketones“, Synthesis 1984, 369.
J. Tsuji, „Addition Reactions with Formation of Carbon-Oxygen Bonds – The Wacker Oxidation and Related Reactions“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 7, 469, Pergamon Press, Oxford, U. K., 1991.
C. Limberg, „On the Trail of CrO2Cl2 in its Reactions with Organic Compounds“, Chemistry – Eur. J. 2000, 6, 2083–2089.
A. Fatiadi, „The Classical Permanganate Ion/Still a Novel Oxidant in Organic Chemistry“, Synthesis 1987, 85.
H. Kropf, E. Müller, A. Weickmann, „Ozone as an Oxidation Agent“, in Methoden Org. Chem. (Houben-Weyl) 4. Aufl., 1952–, Oxidation Part I (H. Kropf, Hrsg.), Bd. 4/1a, 3, Georg Thieme Verlag, Stuttgart, 1981.
H. Heaney, „Oxidation reactions using magnesium monoperphthalate and urea hydrogen peroxide“, Aldrichimica Acta 1993, 26, 35–45.
W. P. Griffith, S. V. Ley, „TPAP: Tetra-n-Propylammonium Perruthenate, a Mild and Convenient Oxidant for Alcohols“, Aldrichimica Acta 1990, 23, 13–19.
S. V. Ley, J. Norman, W. P. Griffith, S. P. Maraden, „Tetrapropylammonium Perruthenate, Pr4N+RuO4–, TPAP: A Catalytic Oxidant for Organic Synthesis“, Synthesis 1994, 639–666.
P. Langer, „Tetra-n-propyl Ammonium Perruthenate (TPAP) – An Efficient and Selective Reagent for Oxidation Reactions in Solution and on the Solid Phase“, J. Prakt. Chem. 2000, 342, 728–730.
N. Rabjohn, „Selenium Dioxide Oxidation“, Org. React. 1949, 5, 331–386.
N. Rabjohn, „Selenium Dioxide Oxidation“, Org. React. 1976, 24, 261–415.
W.-D. Woggon, „Formation of C-O Bonds by Allylic Oxidation with Selenium(IV) Oxide“, in Stereoselective Synthesis (Houben-Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 8, 4947–4956, Georg Thieme Verlag, Stuttgart.
H. Waldmann, „Hypervalent Iodine Reagents“, in Organic Synthesis Highlights II (H. Waldmann, Hrsg.), VCH, Weinheim, New York, 1995, 223–230.
A. Varvoglis (Hrsg.), „Hypervalent Iodine in Organic Synthesis“, Academic, San Diego, CA, 1996.
C. Djerassi, „The Oppenauer Oxidation“, Org. React. 1951, 6, 207–272.
M. Nishizawa, R. Noyori, „Reduction of CpX to CHXH by Chirally Modified Hydride Reagents“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 159, Pergamon Press, Oxford, U. K., 1991.
R. M. Kellogg, „Reduction of CpX to CHXH by Hydride Delivery from Carbon“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 79, Pergamon Press, Oxford, U. K., 1991.
A. L. Wilds, „Reduction with Aluminum Alkoxides (The Meerwein-Ponndorf-Verley Reduction)“, Org. React. 1944, 2, 178–223.
J. Martens, „Formation of C-H Bonds by Reduction of Imino Groups (CpN) “, in Stereoselective Synthesis (Houben-Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 7, 4199–4238, Georg Thieme Verlag, Stuttgart.
R. O. Hutchins, „Reduction of CpN to CHNH by Metal Hydrides“, in Comprehensive Organic Synthesis (B. M. Trost, I. Fleming, Hrsg.), Bd. 8, 25, Pergamon Press, Oxford, U. K., 1991.
R. H. Shapiro, „Alkenes from Tosylhydrazones“, Org. React. 1976, 23, 405–507.
A. R. Chamberlin, S. H. Bloom, „Lithioalkenes from Arenesulfonylhydrazones“, Org. React. 1990, 39, 1–83.
U. Kazmaier, „General (Nondirected) Hydrogenations“, in Stereoselective Synthesis (Houben-Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 7, 4239–4316, Georg Thieme Verlag, Stuttgart.
J. M. Brown, „Directed Hydrogenations“, in Stereoselective Synthesis (Houben-Weyl) 4. Aufl., 1996, (G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Hrsg.), 1996, Bd. E21 (Workbench Edition), 7, 4317–4333, Georg Thieme Verlag, Stuttgart.
H. Adkins, „Catalytic Hydrogenation of Esters to Alcohols“, Org. React. 1954, 8, 1–27.
H. Kumobayashi, „Industrial Application of Asymmetric Reactions Catalyzed by BINAPMetal Complexes“, Rec. Trav. Chim. Pays-Bas 1996, 115, 201–210.
K. Inoguchi, S. Sakuraba, K. Achiwa, „Design Concepts for Developing Highly Efficient Chiral Bisphosphine Ligands in Rhodium-Catalyzed Asymmetric Hydrogenations“, Synlett 1992, 169–178.
C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, „Synthesis and Applications of Binaphthylic C2-Symmetry Derivatives as Chiral Auxiliaries in Enantioselective Reactions“, Synthesis 1992, 503–517.
P. Kocovsky, S. Vyskocil, M. Smrcina, „Non-Symmetrically Substituted 1,1’-Binaphthyls in Enantioselective Catalysis“, Chem. Rev. 2003, 103, 3213–3245.
W. Tang, X. Zhang, „New Chiral Phosphorus Ligands for Enantioselective Hydrogenation“, Chem. Rev. 2003, 103, 3029–3069.
D. J. Ager, S. A. Laneman, „Reductions of 1,3-Dicarbonyl Systems with Ruthenium-Biarylbisphosphine Catalysts“, Tetrahedron Asymmetry 1997, 8, 3327–3355.
S. Otsuka, K. Tani, „Catalytic Asymmetric Hydrogen Migration of Allylamines“ Synthesis 1991, 665–680.
W. S. Knowles, „Asymmetric Hydrogenations (Nobel Lecture)“, Angew. Chem. 2002, 114, 2096–2107; Angew. Chem. Int. Ed. Engl. 2002, 41, 1998–2007.
W. S. Knowles, „Asymmetric Hydrogenations (Nobel Lecture 2001)“, Adv. Synth. Catal. 2003, 345, 3–13.
R. Noyori, „Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001)“, Adv. Synth. Catal. 2003, 345, 15–32.
E. Block, „Olefin Synthesis via Deoxygenation of Vicinal Diols“, Org. React. (N. Y.) 1984, 30, 457.
M. M. Midland, „Asymmetric Reduction with Organoborane Reagents“, Chem. Rev. 1989, 89, 1553.
H. C. Brown, P. V. Ramachandran, „Asymmetric Reduction with Chiral Organoboranes Based on a-Pinene“, Acc. Chem. Res. 1992, 25, 16–24.
V. Ponec, „Selective De-Oxygenation of Organic Compounds“, Rec. Trav. Chim. Pays-Bas 1996, 115, 451–455.
V. K. Singh, „Practical and Useful Methods for the Enantioselective Reduction of Unsymmetrical Ketones“, Synthesis 1992, 607–617.
M. Wills, J. R. Studley, „The Asymmetric Reduction of Ketones“, Chem. Ind. 1994, 552–555. S. Itsuno, „Enantioselective Reduction of Ketones“, Org. React., 1998, 52, 395–576.
R. Noyori, T. Ohkuma, „Asymmetrische Katalyse mit hinsichtlich Struktur und Funktion gezielt entworfenen Molekülen: die chemo- und stereoselektive Hydrierung von Ketonen“, Angew. Chem. 2001, 113, 40–75; „Asymmetric Catalysis by Architectural and Functional Molecular Engineering: Practical Chemo- and Stereoselective Hydrogenation of Ketones“, Angew. Chem. Int. Ed. Engl. 2001, 40, 40–73.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2004 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Brückner, R. (2004). Oxidationen und Reduktionen. In: Reaktionsmechanismen. Springer Spektrum, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45684-2_17
Download citation
DOI: https://doi.org/10.1007/978-3-662-45684-2_17
Published:
Publisher Name: Springer Spektrum, Berlin, Heidelberg
Print ISBN: 978-3-662-45683-5
Online ISBN: 978-3-662-45684-2
eBook Packages: Springer Book Archive