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Synergistic effect in nucleophilic substitution reactions

2009년 8월 28일 16시 14분 02초
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목 16시 : 40분
유기화학 - New Development in Organic Chemistry (Reaction, Methodology, and Synthesis)
저자 및
서강대학교 화학과, Korea
Our continuing interest in the development of fluorination led us to use various ionic liquids (ILs) as both reaction media and phase transfer catalysts, and we found that nucleophilic fluorination is accelerated in ILs. We also reported that tert-alcohol solvents show good performance in nucleophilic fluorination, thereby allowing side reactions to be remarkably suppressed via a weak F-H hydrogen bond, which maintains the inherent nucleophilicity and reduces the basicity of the fluoride anion. The synergistic effect in nucleophilic fluorination was found when we combined two solvents - IL and tert-alcohol – into one molecule. Consequently, these functionalized ILs not only increase the nucleophilic reactivities of the fluoride anion but also remarkably reduce the olefin by-product. Encouraged by a synergistic effect on nucleophilic fluorination, an imidazolium mesylate salt possessing two different solvent properties in one molecule was utilized in various nucleophilic substitution reactions. By a comparison study with 1-n-butyl-3-methylimidazolium ionic liquids, this functionalized IL has proved to be better phase transfer catalyst even under room temperature conditions. It was successfully applied to other nucleophilic substitution reactions such as fluorination, chlorination, bromination, iodination, acetoxylation, azidation, and cyanation.