Page 1152 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1128 Scheme 12.18. Oxidative Cleavage of Carbon-Carbon Double Bonds Using
Transition Metal Oxidants
CHAPTER 12
Oxidations 1 a OsO 4
O CH(CH ) CH O
NaIO 4 2 4
77% as dinitrophenylhydrazone
(DNPH) derivative
2 b H
O
C Ph
OsO 4
IO – N 98%
N 4
CH 3
CH 3
3 c
RuO 4
O O
CH 3 NaIO 4 CH 3
CH CH CH 2 CH CO H
2
2
2
4 d H C CH(CH ) CO H KMnO 4 HO C(CH ) CO H
2 8
2
2
2
2 8
2
IO 4 –
100%
5 e
CH 3 CH 3
CH 3 O H Si(CH ) CH 3 O H O
3 3
O 7 mol % OsO 4 O
3 equiv NaIO 4
t-BuOH, pyridine
C H O O C H O O
2 5
2 5
H H 86%
6 f OCH 3 OCH
CH 3 3
CH 3
OCH 3 5 mol % OsO 4 OCH
O O 3
N 3 equiv NaIO 4 N
CH CH CH CH CH O
(CH ) CH O 2 2 (CH ) CH O 2
3 2
3 2
72%
7 g CH 3 CH 3
KMnO 4 HO CCH CHCHCH CO H
acetone 2 2 2 2
CH 3
CH 3 57%
h Cl
8
F KMnO 4 HO CCF CH CO H
F 2 2 2 2
F
74–80%
9 i CO H
2
HCrO 4
CH CO H
2
2
66–77%
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