Oxidation Methods
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C543 Oxidation
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22 Terms
3 main types of oxidation reagents
Activated DMSO
Chromium-based
Hypervalent Iodine
What is the main reagent used in the Pfitzner-Moffatt oxidation?
Activated DMSO
What activated the DMSO in the Pfitzner-Moffatt reaction?
DCC (dicyclohexylcarboiimide)
What are the typical conditions in the Pfitzner-Moffatt oxidation?
DMSO
DCC with pyridinium trifluoroborate
What is the main problem with the Pfitzner-Moffatt oxidation?
There is a urea byproduct —> difficult to remove
What oxidation mechanism is shown?
Pfitzner-Moffatt
What main reagent is used in the Parikh-Doering reaction?
Activated DMSO
What activates the DMSO in the Parikh-Doering reaction?
Pyridine-SO3 complex
What are the typical conditions used in the Parikh-Doering reaction?
DMSO
NEt3
Pyridine-SO3
What is the main problem with the Parikh-Doering oxidation?
Forms a methylthiomethyl ether byproduct
What mechanism is being shown?
Parikh-Doering
What is the main reagent used in the Swern oxidation?
Activated DMSO
What activates the DMSO in the Swern reaction?
Oxalis chloride
What are the typical conditions for a Swern oxidation?
DMSO
NEt3
Oxalyl chloride
Why is the Swern reaction typically favored over the Pfitzner-Moffatt and the Parikh-Doering oxidations?
In the other oxidations, it is unclear when the activated DMSO has been formed
In the Swern oxidation, the formation of the activated DMSO causes bubbling, indicating its presence
Primary and secondary alcohols are oxidized in high yields + short reaction times
What is the main issue of the Swern oxidation?
Must be run at low temperatures ( below -60 C)
What mechanism is being shown?
Swern
What is the main reagent in the Corey-Kim oxidation?
Activated DMS
What activates the DMS in the Corey-Kim reaction?
NCS (N-chlorosuccinimide)
What are the typical conditions of the Corey-Kim oxidation
SMe2
NEt3
N-chlorosuccinimide (NCS)
Why is the Corey-Kim reaction favored over other activated DMSO reactions?
Can be run at or above -25 C
Primary and secondary alcohols are oxidized in high yield
DMS is easier to dry compared to DMSO
What mechanism is being shown?
Corey-Kim