D.A. Evans Olefin Addition Reactions: Part-3 Chem 206 Bromoniun lons or B-Bromocarbocations in Olefin Bromination. A Kinetic Approach to Product Selectivities httplwww.courses.fasharvardedu/-chem206/ M-F. Ruasse, Accts. Chem. Res. 1990, 23, 87(handout Investigation of the early Steps in Electrophilic Bromination through the emistry 206 Study of the Reaction of Sterically Encumbered Olefins R.S. Brown, Accts. Chem. Res. 1997, 30, 131(handout Advanced Organic Chemistry Predict stereochemical outcome Lecture number 10 Olefin Addition Reactions-3 ■ Olefin Oxymercura Hg(oAc)2, CH2Cl2 Halolactonization 78°cto-20° Simmons -Smith Reaction a Reading Assignment for week 99%, single A. Carey Sundberg: Part B; Chapter 4 Electrophilic Additions to C-C Multilple Bonds 0 Hg(OAc)2, CH2Cl2 Hoveyda, Evans, Fu(1993). Substrate-Directable Chemical 78°to-20° Reactions. Chem. Rev. 93: 1307-70( Handout) XHg S Brown. acc. chem. Res. 1996.30. 131-13 Wednesday Matthew d shair October 9. 2002http://www.courses.fas.harvard.edu/~chem206/ O Me H Me OH Me HO BnO Me O O Me Me Me O Me H Me OH O BnO O O Me Me Me Me Me XHg O Me Me OR Me Me OR Me OH O OH A O OH O Me OR Me Me OR Me Me O D. A. Evans Chem 206 Matthew D. Shair Wednesday, October 9, 2002 ■ Reading Assignment for week Olefin Addition Reactions: Part–3 Chemistry 206 Advanced Organic Chemistry Lecture Number 10 Olefin Addition Reactions–3 ■ Olefin Bromination ■ Olefin Oxymercuration ■ Halolactonization ■ Simmons-Smith Reaction Investigation of the early Steps in Electrophilic Bromination through the Study of the Reaction of Sterically Encumbered Olefins R. S. Brown, Accts. Chem. Res. 1997, 30, 131 (handout) A. Carey & Sundberg: Part B; Chapter 4 "Electrophilic Additions to C–C Multilple Bonds" Hoveyda, Evans, & Fu (1993). Substrate-Directable Chemical Reactions. Chem. Rev. 93: 1307-70 (Handout) Hg(OAc)2, CH2Cl2 -78 oC to -20 oC 85%, dr = 93 : 7 ■ Predict stereochemical outcome 99% 1 16 99%, single diastereomer Hg(OAc)2, CH2Cl2 -78 oC to -20 oC Bromoniun Ions or -Bromocarbocations in Olefin Bromination. A Kinetic Approach to Product Selectivities M-F. Ruasse, Accts. Chem. Res. 1990, 23, 87 (handout) ❋ ❋ R.S. Brown . Acc. Chem. Res. 1996. 30. 131-137