D. A. Evans Pericyclic Reactions: Part-2 Chem 206 ■ Other Reading Materia: http://www.courses.fasharvardedu/-chem206/ aWoodward-Hoffmann Theory R. B. Woodward and R Hoffmann. The Conservation of orbital Symmetry, Verlag Chemie, Weinheim, 1970 Chemistry 206 a Frontier Molecular Orbital Theory Fleming, Frontier Orbitals and Organic Chemical Reactions, Advanced Organic Chemistry John-Wiley and Sons, New York, 1976 IDewar-Zimmerman Theory T. H Lowry and K. S. Richardson, Mechanism and Theory in Lecture number 12 Organic Chemistry, 3rd Ed, Harper&Row, New York, 1987 ■ General Reference R.E. Lehr and A P Marchand, Orbital Symmetry: A Problem Pericyclic Reactions-2 Solving Approach, Academic Press, New York, 1972 ■ Electrocyclic ■ Problems of the Day a Cheletropic Reactions I Sigmatropic Rearrangements: [1, 2 [1,3,[1,5] Predict the stereochemical outcome of this reactio 0 Reading Assignment for week Carey Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions Huisgen, TL, 1964, 3381 Fleming: Chapter 4 Thermal Pericyclic Reactions Houk, et al. Acc. Chem. Res. 1996, 29, 471-477 Suggest a mechanism for the following reaction Houk,et.a.JoC.1996,61,28132825 Meo2C Matthew d shair October 14http://www.courses.fas.harvard.edu/~chem206/ Ph Ph O O O CO2Me CO2Me H H CO2Me MeO2C H H O O O Ph Ph D. A. Evans Chem 206 Matthew D. Shair Monday, Columbus Day, October 14, 2002 ■ Reading Assignment for week: Carey & Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions Pericyclic Reactions: Part–2 Chemistry 206 Advanced Organic Chemistry Lecture Number 12 Pericyclic Reactions–2 ■ Electrocyclic Reactions ■ Cheletropic Reactions ■ Sigmatropic Rearrangements: [1,2], [1,3], [1,5] ■ Other Reading Material: Fleming: Chapter 4 Thermal Pericyclic Reactions ■ Woodward-Hoffmann Theory R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970. ■ Frontier Molecular Orbital Theory I. Fleming, Frontier Orbitals and Organic Chemical Reactions, John-Wiley and Sons, New York, 1976. ■ Dewar-Zimmerman Theory T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, 3rd Ed., Harper & Row, New York, 1987. ■ General Reference R. E. Lehr and A. P. Marchand, Orbital Symmetry: A Problem Solving Approach, Academic Press, New York, 1972. ■ Problems of the Day: Huisgen, TL, 1964, 3381. Predict the stereochemical outcome of this reaction. ❉ heat ❉ Suggest a mechanism for the following reaction. heat Bloomfield, TL, 1969, 3719. Houk, et. al. Acc. Chem. Res. 1996, 29, 471-477. Houk, et. al. JOC. 1996, 61, 2813-2825