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
43
21
14
often
sometimes
avoid
Dess Martin Periodinane
31
20
10
often
sometimes
avoid
MnO
2
(for allylic alcohols, best if you make it yourself!)
12
10
2
often
sometimes
avoid
KMnO
4
13
9
4
often
sometimes
avoid
Ozone
11
10
3
often
sometimes
avoid
TEMPO
7
3
0
often
sometimes
avoid
OsO
4
/NaIO
4
11
11
6
often
sometimes
avoid
PCC
21
21
19
often
sometimes
avoid
Sodium chlorite
5
6
4
often
sometimes
avoid
IBX
11
11
10
often
sometimes
avoid
BaMnO
4
1
0
0
often
sometimes
avoid
Periodic acid/ catalytic PCC/ MeCN
1
2
1
often
sometimes
avoid
TEMPO
12
21
12
often
sometimes
avoid
PDC
8
18
8
often
sometimes
avoid
Jones reagent
6
19
8
often
sometimes
avoid
Air
4
1
6
often
sometimes
avoid
Bobbitt's reagent
5
3
8
often
sometimes
avoid
SO
3
-pyridine (careful with the supplier!)
11
14
14
often
sometimes
avoid
TPAP
12
21
17
often
sometimes
avoid
Periodic acid/ catalytic CrO
3
/ MeCN
2
3
9
often
sometimes
avoid
Cerium(IV)
1
13
14
often
sometimes
avoid
