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Chemistry 550 Syllabus R. Magid Fall 2005 CHEMISTRY 550 SYLLABUS R. MAGID FALL 2005 http://web.utk.edu/~rmagid/index3.html Textbooks: Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994. Smith, M. B.; March, J. March’s Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 5th ed.; John Wiley & Sons: New York, 2001. Syllabus: For each of the topics we will discuss I have listed the following: (1) relevant pages from the texts by Eliel/Wilen/Mander and Smith/March; (2) books and major review articles; (3) pertinent references from the more recent literature; (4) significant articles from the older literature. Although only the reading from the textbooks is required, the interested student may wish to consult the other sources for a deeper understanding of the material. Note: Those books denoted by an asterisk are on reserve in Hodges Library. Many of these books may also be found in the Chemistry Department Reading Room (653) and/or my office. A complete list of the books on reserve is posted at the course web site and on a bulletin board opposite Buehler 416. Readings from these reserve books are not required. Literature: Several recent publications give useful information on how to search the vast chemical literature for compounds, for ideas, for specific authors, etc. Especially recommended, not only for this course but also for your entire graduate school career, are: Wiggins, G. Chemical Information Sources; McGraw- Hill: New York, 1991; a series of articles by Arleen N. Sommerville: "Information Sources for Organic Chemistry, Parts 1 to 3" (which appeared in J. Chem. Educ. 1991, 69, 553, 842; 1992, 69, 379); and "Subject Searching of Chemical Abstracts Online" (which appeared in J. Chem. Educ. 1993, 70, 200.) Also, Appendix A (pp. 1605-1639) of Smith/March gives instructions on searching the literature. Abbreviations for Journals AA: Aldrichimica Acta AAC: Advances in Alicyclic Chemistry AC: Acta Crystallographica ACR: Accounts of Chemical Research ACS: Acta Chemica Scandinavica AJC: Australian Journal of Chemistry Ang: Angewandte Chemie, International Edition (English) Ann: Justus Liebigs Annalen der Chemie APO: Advances in Physical Organic Chemistry ATIM: Advances in Theoretically Interesting Molecules BSB: Bulletin des Sociétés Chimiques Belges BSF: Bulletin de la Société Chimique de France BSJ: Bulletin of the Chemical Society of Japan CB: Chemische Berichte CBr: Chemistry in Britain CC: Chemical Communications, Chemical Society, London CCC: Collection of Czechoslovak Chemical Communications CEJ: Chemistry: A European Journal CEN: Chemical and Engineering News Chi: Chimia CJC: Canadian Journal of Chemistry CL: Chemical Letters CPL: Chemical Physics Letters CR: Chemical Reviews CS: Chemica Scripta CSR: Chemical Society Reviews CT: Chemical Technology 2 EJO: European Journal of Organic Chemistry FCF: Fortschritte der Chemischen Forschung GCI: Gazzetta Chimica Italiana HCA: Helvetica Chimica Acta CEJ: Chemistry European Journal Het: Heterocycles IC: Inorganic Chemistry IJC: Israel Journal of Chemistry IJK: International Journal of Chemical Kinetics JACS: Journal of the American Chemical Society JCC: Journal of Computational Chemistry JCE: Journal of Chemical Education JCF(I) or (II): Journal of the Chemical Society, London, Faraday Transactions, Part I or Part II JCP: Journal of Chemical Physics JCR(S): Journal of Chemical Research (Synopses) JCS(I) or (II): Journal of the Chemical Society, London, Perkin Transactions, Part I or Part II JCT: Journal of Chemical Thermodynamics JMS: Journal of Molecular Structure JMS(Th): Journal of Molecular Structure (Theochem) JOC: Journal of Organic Chemistry JPC: Journal of Physical Chemistry JPC(A) or (B) Journal of Physical Chemistry, Part A or Part B JPO: Journal of Physical Organic Chemistry JTh: Journal of Molecular Structure (Theochem) Nat: Nature NJC: Nouveau Journal de Chimie OBC: Organic & Biomolecular Chemistry OL: Organic Letters OMR: Organic Magnetic Resonance OMS: Organic Mass Spectrometry OR: Organic Reactions Org: Organometallics PAC: Pure and Applied Chemistry PCCP: Physical Chemistry Chemical Physics PNA: Proceedings of the National Academy of Sciences PPO: Progress in Physical Organic Chemistry QR: Quarterly Reviews RCR: Russian Chemical Reviews RTC: Recueil des Travaux Chimiques des Pays-Bas SA: Scientific American SC: Synthetic Communications Sci: Science SL:Synlett SPC: Survey of Progress in Chemistry Syn: Synthesis TCC: Topics in Current Chemistry Tet: Tetrahedron Tet(A): Tetrahedron Asymmetry TL: Tetrahedron Letters TS: Topics in Stereochemistry ZOK: Zhurnal Organicheskoi Khimii I. Bonding, Resonance, and Simple Hückel Theory A.General Discussions 1. Smith/March: pp. 3-24, 32-45, (45-77 optional). 2. Hoffmann, Shaik, Hiberty, ACR, 36, 750 (2003) 3 2. Hand-outs a. Electronic Structure of First Row Elements. b. Bonding in Organic Compounds. c. Formal Charges on Atoms; Resonance Contributing Structures. d. Stereochemical Definitions. e. New Stereochemical Definitions. f. Grasping the Concepts of Stereochemistry (assignment of R and S configuration). g. Chem. 360 Handout (Formal Charges, Curved Arrow, Resonance). 3. a. *G. Wheland, "Resonance in Organic Chemistry." b. *Roberts, "Notes on Molecular Orbital Calculations." c. *Liberles, "Introduction to Molecular Orbital Theory." d. *Borden, "Modern Molecular Orbital Theory for Organic Chemists." e. *Zimmerman, "Quantum Mechanics for Organic Chemists." f. *Dewar, "Molecular Orbital Theory of Organic Chemistry." g. *Streitwieser, "Molecular Orbital Theory for Organic Chemists." h. *Yates, "Hückel Molecular Orbital Theory." i. *Coulson, O'Leary, and Mallion, "Hückel Theory for Organic Chemists." j. *Salem, "Electrons in Chemical Reactions. First Principles." k. *Isaacs, "Physical Organic Chemistry" Chap 1. l *Pross, "Theoretical and Physical Principles of Organic Reactivity," Chap 1-4. m. *Jean and Volatron, "An Introduction to Molecular Orbitals" II. Conformational Analysis A. General Discussions 1. Smith/March: pp. 125-141, (141-144 optional), 144-147, (147-160 optional), 160-191. 2. *Eliel/Wilen/Mander: pp. 1-8, (11-20 optional), 20-24, 50-69, (72-97 optional), 539-550, 507-606, (606-615, 665-685 optional), 686-720, 776-785, 1119-1125, (1125-1138 optional), 1138-1148, 1163-1166, 1172-1175. 3. *Eliel, et al., "Conformational Analysis." 4. *Hanack, "Conformation Theory." 5. *Gunstone, "Guidebook to Stereochemistry." 6. *Ramsay, "van't Hoff-LeBel Centennial." 7. *Chiurdoglu, "Conformational Analysis: Scope and Present Limitations." 8. *Nogradi, "Stereochemistry. Basic Concepts and Applications." 9. *Ramsay, "Stereochemistry," Chap 12-14. 10. *Maskill, "The Physical Basis of Organic Chemistry," Chap 1 and 2. 11. *Kalsi, "Stereochemistry: Conformation and Mechanism" 12. *Nasipuri, "Stereochemistry of Organic Compounds." 13. *Juaristi, "Introduction to Stereochemistry and Conformational Analysis." 14. *Juaristi, "Conformational Behavior of Six-Membered Rings" 15. *Oki, "The Chemistry of Rotational Isomers." 16. *Dodziuk, "Modern Confromational Analysis" 17. *Robinson, "Organic Stereochemistry" B. Rotational Barrier in Ethane, Butane, and Related Molecules. 1. Allinger, JACS, 93, 1637 (1971); 99, 3282, 8127 (1977); 104, 6272 (1982); Tet, 30, 1579 (1974); JACS, 111, 8551, 8561, 8576 (1989); 112, 114 (1990). 2. Wiberg, JACS, 110, 8029 (1988); 112, 6531 (1990); JPC, 94, 6956 (1990). 3. Schleyer, Mislow, JACS, 114, 6791 (1992). 4. Allinger, Schaefer, JCP, 106, 5143 (1997). 5. Michl, JACS, 120, 573 (1998). 6. Goodman, ACR, 33, 983 (1999); Nat, 411, 565 (2001). 7. Inagaki, JACS, 123, 1193 (2001). 8. Deleuze, JACS, 123, 4049 (2001). 9. Bickelhaupt, Ang, 42, 4183 (2003). 10. Weinhold, Ang, 42, 4188 (2003). 11. Mo, Ang, 43, 1986 (2004). 4 C. Chiral Compounds without Stereogenic Centers. 1. General a. Farina, Tet, 30, 1819 (1974). b. Nakazaki, TS, 15, 200 (1984). c. Misiti, ACR, 28, 163 (1995). d. Katz, Ang, 39, 1921 (2000). e. Fujita, BSJ, 75, 1863, 1949 (2002). 2. Biphenyls and Related Compounds a. Bringmann, Ang, 29, 977 (1990); JOC, 65, 722 (2000). b. König, Ann, 781 (1995); 377 (1996). c. Mitchell, TL, 38, 6517 (1997). d. Havlas, JOC, 68, 5677 (2003). e. Nori-shargh, JMS(Th), 717, 41 (2005). 3. Allenes and Spirans a. Yavari, JCR(S), 110 (1994); JMS, 309, 53 (1994); 393, 167 (1997); JMS(Th), 465, 156 (1999). b. Kitching, JOC, 68, 3739 (2003). c. Krause, Ang, 43, 1196 (2004). 4. trans-Cycloalkenes a. Liebman, CR, 76, 311 (1976). b. Marshall, JACS, 102, 3287 (1980); 104, 7430 (1982); 106, 723 (1984); Tet, 42, 1703 (1986). c. Inoue, JCS(II), 1672, 1678 (1980); CC, 1031 (1981); JACS, 111, 6480 (1989); JOC, 57, 1332 (1992); 58, 1011 (1993); JCS(II), 2057 (1995); CC, 2627 (1996); JACS, 119, 472 (1997); 121, 9877, 10702 (1999); 122, 406 (2000); CC, 251 (2000); OBC, 1, 4435 (2003). d. Noe, JACS, 118, 2821 (1996); JOC, 64, 4580 (1999). 5. Helicenes a. Vögtle, Tet(A), 7, 109 (1996) b. Katz, JACS, 119, 10054 (1997); 121, 79 (1999); JOC, 64, 302, 3671 (1999); 65, 806, 815, 1850 (2000); 69, 7769 (2004). c. Stara, JOC, 63, 4046 (1998); TL, 40, 1993 (1999). d. Alrichs, JACS, 122, 1717 (2000). e. Avnir, Tet(A), 12, 645 (2000). f. Yamaguchi, JOC, 66, 557 (2001). g. Soai, Ang, 40, 1096 (2001). h. Urbano, Ang, 42, 3986 (2003). i Weber, EJO, 2872 (2003). D. Cyclohexane and Monosubstituted Derivatives, Conformational Analysis 1. Strauss, JCE, 48, 221 (1971); JACS, 103, 1001 (1981). 2. Wiberg, JACS, 94, 8426 (1972); JOC, 64, 2085, 6387 (1999); 65, 1181 (2000). 3. Chapman, Anet, JACS, 97, 3244 (1975). 4. Allinger,
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