General Procedure for Oxidation of Alcohols with IBX

The alcohol is added3 to a ca. 0.4—1 M solutionb of ca. 1-10 equivalents— typically 1.1 3 eq.—of IBXC in DMSO.d,e In the oxidation of substrates containing a primary or secondary amine, ca. 1 1.5 equivalents of an acid such as TFA must be added for protection. When a TLC analysis shows that most of the starting compound is consumed/ the reaction is elaborated according to two alternative protocols  

The reaction mixture is filtered and concentrated, affording a crude product that may need further purification. This very simple work-up is 

83 In this very remarkable oxidation in which the primary amine is protected by protonation with TFA, the reaction succeeds in spite of the presence of a primary amine and the tendency of the molecule to suffer an oxidative C-C bond breakage.  

---