ORGANIC CHEMISTRY Chapter 8 8. 9C Carbenoids The Simmons-Smith Cyclopropane Synthesis CH2I2 Zn( Cu)- ICh,ZnI=: CH A carbenoid Zn(Cu) t ch CH Et,o Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 8.9C Carbenoids: The Simmons-Smith Cyclopropane Synthesis CH2I2 + Zn(Cu) ICH2ZnI = CH2 A carbenoid + CH2I2 CH2 Zn(Cu) Et2O H H
ORGANIC CHEMISTRY Chapter 8 8.10 Oxidation of Alkenes: Syn Hydroxylation Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 8.10 Oxidation of Alkenes: Syn Hydroxylation
ORGANIC CHEMISTRY Chapter 8 0 OH CC=C\+KMnO cold 111 C-C OH HO A.2-Dic (1)OsO4, pyridine CH3CH=CH CHrCH-CH (2)Na2 SO3/H2O or naSO,/ho HO OH Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 C C C C HO OH + KMnO4 cold OH , H2O A 1,2-Diol CH3CH CH2 (1) OsO4, pyridine (2) Na2SO3 / H2O or NaHSO3 / H2O CH3CH CH2 HO OH
ORGANIC CHEMISTRY Chapter 8 8. 10A Mechanism for Syn Hydroxylation of alkenes cold HO H H HO OH M Mn OK OK cis-1, 2-Cyclohexanediol EtO H,O or THF H H HO OH Os cis-1, 2-Cyclohexanediol Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 8.10A Mechanism for Syn Hydroxylation of Alkenes Mn O O OK O cold H H Mn O O OK O HO OH H H cis-1,2-Cyclohexanediol H2O Os O O O O H H Os O O H2O HO OH H H cis-1,2-Cyclohexanediol O O or THF Et2O
ORGANIC CHEMISTRY Chapter 8 Anti Hydroxylation OH RCO2H HO C—C C—C C=C H or oH OH oxirane, epoxide 环氧化合物 RCO3 h Peroxycarboxylic acid过氧酸 CH3C-O-OH CF3C-0-OH C-0-0H C-O-OH 33%H2O2 CH2C-OH CH2C-O-OH H Department of Chemistry, Xiamen University
ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 8 Anti Hydroxylation Anti Hydroxylation C C C C O 环氧化合物 oxirane , epoxide RCO3H H2O H or OH C C OH OH RCO3H Peroxycarboxylic acid 过氧酸 CH3C OH O 33% H2O2 CH3C O O OH H+ CH3C O O OH CF3C O O OH C O OH O C O OH Cl O