The Tour of Collective Wisdom presents:
Desert Island Oxidations
Choosing oxidation conditions can be overwhelming. Here is a list of popular choices.
Oxidation:
I often use this
I sometimes use this
I avoid this
Verification:
Oxidation
Use this often
Use this sometimes
Avoid using this
I use this...
Swern
52
26
20
often
sometimes
avoid
Dess Martin Periodinane
40
28
10
often
sometimes
avoid
Ozone
15
16
4
often
sometimes
avoid
MnO
2
(for allylic alcohols, best if you make it yourself!)
14
15
4
often
sometimes
avoid
KMnO
4
17
11
8
often
sometimes
avoid
TEMPO
21
28
14
often
sometimes
avoid
OsO
4
/NaIO
4
13
14
9
often
sometimes
avoid
mCPBA
5
3
1
often
sometimes
avoid
PCC
27
24
25
often
sometimes
avoid
PDC
10
22
8
often
sometimes
avoid
Selenium dioxide (allylic oxidation)
1
0
0
often
sometimes
avoid
Hydrogen Peroxide
0
1
0
often
sometimes
avoid
Sodium chlorite
7
13
8
often
sometimes
avoid
RuCl
3
·nH
2
O/NaIO
4
0
5
1
often
sometimes
avoid
Jones reagent
7
23
9
often
sometimes
avoid
TPAP
16
23
18
often
sometimes
avoid
SO
3
-pyridine (careful with the supplier!)
14
14
16
often
sometimes
avoid
Air
6
4
9
often
sometimes
avoid
BaMnO
4
1
7
4
often
sometimes
avoid
IBX
12
14
17
often
sometimes
avoid
Bobbitt's reagent
6
5
12
often
sometimes
avoid
Periodic acid/ catalytic PCC/ MeCN
2
2
11
often
sometimes
avoid
Periodic acid/ catalytic CrO
3
/ MeCN
3
3
13
often
sometimes
avoid
print qq~
