Chapter 13

Oxidation Reactions

 
Collins reagent can be prepared and isolated or generated in situ.
  • Collins reagent is the mixture of chromium trioxide with pyridine in dichloromethane.
Isolation of reagent often leads to improved yields.
It is used to selectively oxidize primary alcohols to aldehyde, and will tolerate many other functional groups in the molecule.
It can be used as an alternative to Jones reagent and PCC in oxidation of secondary alcohols. Moreover, Collins reagent is especially useful for oxidations of acid sensitive compounds.
This complex is both difficult and dangerous to prepare, as it is very hygroscopic and can inflame during its preparation.
It is required to be used in a sixfold excess in order to complete the reaction.
One of the steps in the synthesis of prostaglandin F2α employs Collin’s reagent as oxidant.
Corey E J, JACS, 1969, 91, 5675