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Stanford University
CHEM 255: Advanced Inorganic Chemistry - Syllabus Spring 2007 |
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Honor Code
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HTML Document | 19 Mar 2007 |
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Chemistry 255
Principles of Organotransition Metal Chemistry - Spring 2007 - Instructor: Professor Robert M. Waymouth Stauffer I, Room 205, Phone: 723-4515, E-mail: waymouth@stanford.edu Office Hours: Monday 3:00 pm - 4:00 pm, or by arrangement. T.A.: Wonhee Jeong Stauffer I, Room 208, Phone: 723-8029, E-mail: wonhee@stanford.edu Office Hours: Friday 11:00 am - 12:15 pm, or by arrangement Lecture: MW 11:00 am - 12:15 pm Texts: The Organometallic Chemistry of the Transition Metals, 4th Ed., Crabtree, Wiley, 2005. (Optional) Principles and Applications of Organotransition Metal Chemistry, 2nd Ed., Collman, Hegedus, Norton and Finke (CHNF). 1987. Organometallic Chemistry, Spessard and Miessler, Prentice Hall, 1997. Objective: This course is an introduction to the structure, bonding and reactivity of organotransition metal compounds. Aspects of this extremely active research area that will be covered are indicated on the attached course outline. The focus of the presentation will be on physical organometallic chemistry, with an emphasis on the mechanisms of organometallic transformations and methods for their elucidation. We will cover some of the fundamental reaction types of organotransition metal complexes including: oxidative addition/reductive elimination, migratory insertion, attack on coordinated ligands, and reactivity of metallacycles, carbenes, and carbynes. The course will also focus on applications of organotransition metal complexes in catalysis and in organic chemistry. Examinations There will be one final exam, problems sets and a term paper in this course. and Grading: The term paper is due: Wednesday, May 30, 2007 The final exam will be on: Friday, June 8, 2007 (8:30 am) The grading in this course will be determined from the final exam (30%), the term paper (30%), and the problem sets (40%). This course may be taken + / NC provided appropriate arrangements have been made with the registrar. Assignments: Suggested reading assignments are given in the attached course syllabus. You are encouraged to consult other books and sources for information, including textbooks on reserve and reviews cited in the lecture notes. We will likely deviate from the course schedule, but the syllabus provides a general outline of material to be covered in the course. Problem sets will be provided as handouts approximately every other week. Material in the problem sets will often not be covered in lecture or in your text. You should feel free to use the primary literature, textbooks on reserve, or Swain library should you need additional information. Problem sets, lecture notes and solutions to the problems will be posted on coursework. http://coursework.stanford.edu Chem255, Spring 2007 Principles of Organotransition Metal Chemistry Week 1 L1: 4/4 Structure and Bonding, 18 Electron Rule Formal Oxidation State, Ligand Substitution (Chpt. 1-5) Week 2 L2: 4/9 Ligand Substitution, Oxidative Addition (Chpt. 4, 6) L3: 4/11 Week 3 L4: 4/16 Oxidative Addition (Chpt. 6) L5: 4/18 PBLM SET 1 DUE Reductive Elimination (Chpt. 6) Week 4 L6: 4/23 Migratory Insertion (Chpt. 7) L7: 4/25 Attack on Coordinated Ligands (Chpt. 8) Week 5 L8: 4/30 Cross-coupling (Chpt. 9.6, Spessard Chpt. 11.3) L9: 5/2 PBLM SET 2 DUE Kumada, Stille, Suzuki & Heck Reactions (handouts) Week 6 L10: 5/7 Cross-coupling (handouts) L11: 5/9 Hydrogenation (Chpt. 9.2) Week 7 L12: 5/14 Hydrogenation (Chpt. 9.2) L13: 5/16 PBLM SET 3 DUE Hydroformylation (Chpt. 9.3) Week 8 L14: 5/21 Olefin Polymerization (Chpt. 12.2) L15: 5/23 Week 9 5/28 Memorial Day, no class L16: 5/30 Term Paper Due Reactions of Carbenes, Metathesis (Chpt. 11, Chpt. 12.1) Carbometallation, Cyclization Reactions (Chpt. 11) Week 10 L17: 6/4 Oxidation (Chpt. 14.2) L18: 6/6 PBLM SET 4 DUE 6/8 FINAL EXAM (8:30 am - 11:30 am) Chemistry 255 Principles of Organotransition Metal Chemistry - Spring 2007 - TERM PAPER DUE WED MAY 30, 2007 Assignment: The term paper for this course should address some aspect of organotransition metal chemistry. Some representative topics for the term paper are given below. The topic for your term paper should be discussed with me and indicated on your problem set due May 2. You are not restricted to the topics listed below. Included in the term paper should be a brief historical perspective on the area, your own perspective on the significance, or lack thereof, of the topic, and a critical evaluation of the seminal work (rather than a laundry list of all work) in the area. The term paper should also address unresolved issues and your own perspective on new research opportunities in the area. A simple literature review of the area will not suffice for an A grade, as I am looking for your critical evaluation of the topic. The length of the paper is less important than the content. A lengthy, rambling review will be graded more severely than a short concise one that covers all the bases. I would imagine that ≤ 8 pages would suffice. Topics: Dihydrogen Complexes C-H Activation in Organic Synthesis Metathesis Polymerization C-C Bond Activation Methane Activation and Conversion Enantioselective Hydroformylation Enantioselective Epoxidation Catalytic Aziridination Organometallic Electrocatalysis CO2 Activation Catalysis for Fuel Cells CO/Olefin Copolymerization Functional Diene Dimerization / Oligomerization Catalytic Enantioselective C-C Bond Formation Radical C-H Activation Organometallic Approaches to Coal Gasification Reduction of CO to C2 Feedstocks The Shell Higher Olefin Process / FEAST Technology Catalytic Trimerization of Ethylene Catalytic Hydroamination Polymerization with Late Metal Catalysts Carbonylation of Alkenes and Alkynes Catalytic Amination, Etherification (Hartwig / Buchwald Couplings) Catalytic Atom Transfer (Amination, Osmylation, Amino-Hydroxylation) Texts on Reserve: Boor, J., “Ziegler-Natta Catalysts and Polymerizations” Call number: TP159.C3 B66 1979 Collman, J. P. et al., “Principles and Applications of Organotransition Metal Chemistry” Call number: QD411.C641 1987 Cornils and Herrmann, “Applied Homogeneous Catalysis with Organometallic Compounds” Call number: QD505.A67 1996 Crabtree, R.H., “The Organometallic Chemistry of the Transition Metals” Call number: QD411.8.T73 C73 2001 Dickson, “Homogeneous Catalysis with Complexes of Rhodium and Iridium.” Call number: QD505.D53 1985 Didier, A., “Electron Transfer and Radical Processes in Transition - Metal Chemistry” Call number: QD172.T6 A88 1995 Espenson, J. H., “Chemical Kinetics and Reaction Mechanisms” Call number: QD502.E86 1995 Hegedus, L. S., “Transition Metals in the Synthesis of Complex Organic Molecules” Call number: QD262.H35 1999 Ivin, K. J., “Olefin Metathesis and Metathesis Polymerization” Call number: QD305.H7 I952 1997 Jordan, R. B., “Reaction Mechanisms of Inorganic and Organometallic Systems” Call number: QD502.J67 1991 Masters, C., “Homogeneous Transition-Metal Catalysis: A Gentle Art” Call number: QD172.T6 M33 1981 Negishi, E., “Handbook of Organopalladium Chemistry for Organic Synthesis” Vol. 1, 2 Call number: QD 412.P4 H36 2002 Noyori, R., “Asymmetric Catalysis in Organic Synthesis” Call number: QD262.N69 1994 Ojima, I., “Catalytic Asymmetric Synthesis” Call number: TD262.O35 2000 Parshall, G. W. and Ittel, S. D., “Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes” Call number: QD505.P37 1992 Tobe, M. L. and Burgess, J., “Inorganic Reaction Mechanisms”. Call number: QD502.5.T63 1999 Yamamoto, A., “Organotransition Metal Chemistry: Fundamental Concepts and Applications” Call number: QD411.Y3613 1986 |
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