Hydroxamate anions bound to partially laurylated poly(2-ethyl-1-vinylimidazole) were found to serve as excellent catalysis for proton abstraction from α-ketols. Proton removal from benzoin by N-methylmyristohydroxamate anion in the presence of the polymer (lauryl group content, 29 mol%) was 2.1×104 times faster than the corresponding reaction in the absence of the polymer, and 330 times faster than that by hydroxide ion. The maximum catalytic efficiency existed at ca. 30-mol% lauryl group content. Addition of KCl and ethanol significantly suppressed the reaction. Thus, hydroxamate—polymer complexes would act generally as excellent base catalysts for proton abstraction to form the carbanion intermediates.
All Science Journal Classification (ASJC) codes
- Polymers and Plastics
- Materials Chemistry