Epoxide cat. ROOR Anti- Markovnikov addition 1)OsO4 2)NaHSO3, H2O Halogenation Syn Addition Hydroboration- Oxidation Anti Dihydroxylation Anti Addition Hydrohalogenation H2SO4, H2O Br2 or Cl2 Acid- catalyzed hydration Pd, Pt Nucleophiles or Bases Catalytic Hydrogenation Halogen (Br + Cl) and H2O Bromonium ion 1) BH3, THF 2) NaOH, H2O2 HBr, HCl, HI Markovnikov addition Syn Dihydroxylation Halohydrin formation 1) RCO3H 2) H3O+ Epoxide cat. ROOR Anti- Markovnikov addition 1)OsO4 2)NaHSO3, H2O Halogenation Syn Addition Hydroboration- Oxidation Anti Dihydroxylation Anti Addition Hydrohalogenation H2SO4, H2O Br2 or Cl2 Acid- catalyzed hydration Pd, Pt Nucleophiles or Bases Catalytic Hydrogenation Halogen (Br + Cl) and H2O Bromonium ion 1) BH3, THF 2) NaOH, H2O2 HBr, HCl, HI Markovnikov addition Syn Dihydroxylation Halohydrin formation 1) RCO3H 2) H3O+
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G-Epoxide
I-cat. ROOR
N-Anti-Markovnikov addition
O-1)OsO4
2)NaHSO3, H2O
O-Halogenation
G-Syn Addition
I-Hydroboration-Oxidation
N-Anti Dihydroxylation
B-Anti Addition
G-Hydrohalogenation
G-H2SO4, H2O
O-Br2 or Cl2
G-Acid-catalyzed hydration
O-Pd, Pt
O-Nucleophiles or Bases
B-Catalytic Hydrogenation
B-Halogen (Br + Cl) and H2O
I-Bromonium ion
B-1) BH3, THF
2) NaOH, H2O2
B-HBr, HCl, HI
I-Markovnikov addition
I-Syn Dihydroxylation
N-Halohydrin formation
N-1) RCO3H
2) H3O+