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 alpha,omega-di(2-methyl-2,3-epoxypropyl)polyisobutylene are reported. The epoxidation of alpha,omega-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 H-1 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 alpha,omega-di(2-methyl-3-hydroxylpropyl)polyisobutylene with high efficiency. (C) 2002 Wiley Periodicals, Inc.