Oxidative cleavage of vicinal diols: IBX can do what Dess-Martin periodinane (DMP) can.
The fact that IBX exhibits reactivity akin to DMP is demonstrated from the results observed with strained and sterically hindered syn 1,2-diols, which undergo oxidative cleavage via a 12-I-5 spirobicyclic periodinane. The use of TFA, a protonating solvent, promotes the formation of the 12-I-5 intermediate for 1,2-diols of all types (sec,sec, sec,tert and tert,tert), leading to efficient oxidative fragmentation.
Moorthy
Jarugu Narasimha
JN
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. moorthy@iitk.ac.in
Singhal
Nidhi
N
Senapati
Kalyan
K