- 作者: 謝瑞隆 ; 林瑞莉 ; 黃建智 ; 卓靜哲
- 作者服務機構: Department of Chemistry, National Cheng Kung University, Taiwan, R.O.C.
- 中文摘要: The kinetics of the substitution reactions of triphenylphosphine (TP) with chlorobenzyl chlorides (CBC), 2,5-dimethylbenzyl chloride (DMBC), and methylbenzyl bromides (MBB) in aprotic organic solvent was studied under the extraction by water. The effects of water, agitation, organic solvent, reactant, and temperature were investigated. These reactions take place via the SN2 mechanism and exhibit large and negative entropy of activation. The order of relative activity of solvents is CHCl3 > CH2Cl2 >> C6H6. In CHCl3, the order of relative reactivity of benzyl chloride (BC), benzyl bromide (BB), CBC, DMBC, and MBB toward reaction with TP is 2-MBB >4-MBB > 3-MBB > BB > DMBC > BC > 2-CBC > 4-CBC > 3-CBC. These reactions produce quantitatively benzyltriphenylphosphonium salts, which are useful for synthesizing Z-form isomers of stilbenes via the two-phase Wittig reaction.
- 英文摘要: --
- 中文關鍵字: Triphenylphosphine; Chlorobenzyl Chloride; Methylbenzyl Bromide; Dimethylbenzyl Chloride; Substitution Reaction; Solvent Effect; Kinetics
- 英文關鍵字: 三苯基膦;氯苯甲基氯化物;甲基苯甲基溴化物;二甲基苯甲基氯化物;取代反應;溶劑效應;動力學