D. A. Evans Pericyclic Reactions: Part-3 Chem 206 Other Reading material http://www.courses.fasharvardedu/-chem206/ [2, 3]Sigmatropic Rearrangements Chemistry 206 Nakai, T Mikami, K. Org. React(NY. 1994, 46, 105-209 Hoffmann, Angew. Chem. Int. Ed 1979, 18, 563-572(Stereochemistry of) Advanced Organic Chemistry Nakai, Chem. Rev. 1986, 86, 885-902 (Wittig Rearrangement) Evans. Accts. Chem. Res 7, 147-55 Sulfoxide Rearrangement Vedejs, Accts. Chem. Res. 1984, 17, 358-364(Sulfur Ylilde Rearrange Lecture Number 13 [3, 3]Sigmatropic Rearrangements Trost, Ed, Comprehensive Organic Synthesis 1992, Vol 5, Pericyclic Reactions-3 Chapter 7.1:( Cope, oxy-Cope, Anionic oxy-Cope Chapter 7. 2, Claisen I Introduction to Sigmatropic Rearrangements S.J. Rhoades, Organic Reactions 1974, 22, 1( Cope, Claisen a 2, 3] Sigmatropic Rearrangements S.R. Wilson, Organic Reactions 1993, 43, 93 (oxy-Cope T.S. Ho, Tandem Organic Reactions 1992, Chapter 12(Cope, Claisen) Paquette, L A (1990) controlled construction of complex cyclic Reading Assignment for week ketones by oxy-Cope gement. Angew. Chem., Int. Ed Engl. 29: 609 Carey Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions Fleming: Chapter 4 ■ Problems of the Day Thermal Pericyclic reactions Provide a mechanism for this transformation Evans, et al. Acc. Chem. Res. 1974. 7. 149-155 Wednesday Matthew d shair October 16. 2002 For study on this 2, 3 rxn See Baldwin JACS 1971, 93, 6307http://www.courses.fas.harvard.edu/~chem206/ Me Me S Me Me S PPh3 S=PPh3 Me Me S Me Me D. A. Evans Chem 206 Matthew D. Shair Wednesday, October 16, 2002 ■ Reading Assignment for week: Carey & Sundberg: Part A; Chapter 11 Concerted Pericyclic Reactions Pericyclic Reactions: Part–3 Chemistry 206 Advanced Organic Chemistry Lecture Number 13 Pericyclic Reactions–3 ■ Introduction to Sigmatropic Rearrangements ■ [2,3] Sigmatropic Rearrangements ■ Other Reading Material: Fleming: Chapter 4 Thermal Pericyclic Reactions ■ Problems of the Day: [2,3] Sigmatropic Rearrangements Trost, Ed., Comprehensive Organic Synthesis 1992, Vol 6, Chapter 4.6: Nakai, T.; Mikami, K. Org. React. (N.Y.) 1994, 46, 105-209. Hoffmann, Angew. Chem. Int. Ed. 1979, 18, 563-572 (Stereochemistry of) Nakai, Chem. Rev. 1986, 86, 885-902 (Wittig Rearrangement) Evans, Accts. Chem. Res. 1974, 7, 147-55 (Sulfoxide Rearrangement) Vedejs, Accts. Chem. Res. 1984, 17, 358-364 (Sulfur Ylilde Rearrangements) [3,3] Sigmatropic Rearrangements Trost, Ed., Comprehensive Organic Synthesis 1992, Vol 5, Chapter 7.1: (Cope, oxy-Cope, Anionic oxy-Cope) Chapter 7.2, Claisen S. J. Rhoades, Organic Reactions 1974, 22, 1 (Cope, Claisen) S. R. Wilson, Organic Reactions 1993, 43, 93 (oxy-Cope) T. S. Ho, Tandem Organic Reactions 1992, Chapter 12 (Cope, Claisen) Paquette, L. A. (1990). “Stereocontrolled construction of complex cyclic ketones by oxy-Cope rearrangement.” Angew. Chem., Int. Ed. Engl. 29: 609. For study on this [2,3] rxn See Baldwin JACS 1971, 93, 6307 heat Provide a mechanism for this transformation. Evans, et al. Acc. Chem. Res. 1974, 7, 149-155