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HX
MK
Rearrangements Possible

HBr (ROOR)
Anti-MK

H+/H2O or Dilute Acid
MK
Rearrangements Possible

1) H2O, Hg(OAc)2
2) NaBH4
Anti
MK
No Rearrangement

1) CH3OH, Hg(OAc)2
2) NaBH4
Anti
MK
No Rearrangement

1) BH3, THF
2) H2O2, OH
Syn
Anti-MK

X2 (Cl, Br, I)
Anti

Br2
H2O
Anti
MK

H2 + (Pt, Pd, or Ni)
Syn

CH2N2 + UV
(or ICH2ZnI)

CHBr3
KOH/H2O

ROOOH (Peroxy Acid)
(or MCPBA)

H+/H2O (added after MCPBA)
Anti-diol

OsO4, H2O2 (or Cold dilute KMnO4, OH-)
Syn

Warm concentrated KMnO4

Warm concentrated KMnO4 (terminal C)

O3
CH3—S—CH3

O3
KMnO4
