Dimethyldioxirane as a new and effective oxidation agent for the epoxidation of α,ω‐di(isobutenyl)polyisobutylene: A convenient synthesis of α,ω‐di(2‐methyl‐3‐hydroxypropyl)‐polyisobutylene

The synthesis and characterization of α,ω‐di(2‐methyl‐2,3‐epoxypropyl)polyisobutylene are reported. The epoxidation of α,ω‐di(isobutenyl)polyisobutylene was achieved at room temperature with dimethyldioxirane, which proved to be a very effective reagent for epoxidation without the formation of byproducts. A very good agreement was found for the conversion determined by 1H NMR and matrix‐assisted laser desorption/ionization mass spectrometry (MALDI HMS). The epoxy end groups were converted quantitatively into aldehyde termini with zinc bromide as a catalyst. The aldehyde groups were then reduced with LiAlH4 into primary hydroxyl functions to obtain α,ω‐di(2‐methyl‐3‐hydroxylpropyl)polyisobutylene with high efficiency.