“…Moreover, since the early days of crown-ether chemistry, 18-crown-6 has been used to enhance the solubility of reactive potassium salts in organic media, e.g. KMnO 4 (Doheny & Ganem, 1980). [K(18c6)]OAc (OAc = acetate) has been shown to be useful as an acetylation agent for alkyl halides (Liotta et al, 1974), and over the past few years 'CECILs' (crown ether complex cation ionic liquids) such as [K(18c6)]OAc and [K(18c6)]OH gained in importance as basic catalysts for various organic transformations (e.g.…”
Hydrogen bonding plays an important role in the structures of two solvated forms of [K(18c6)]OAc (18c6 = 18-crown-6 = 1,4,7,10,13,16-hexaoxacyclooctadecane and OAc = acetate).
“…Moreover, since the early days of crown-ether chemistry, 18-crown-6 has been used to enhance the solubility of reactive potassium salts in organic media, e.g. KMnO 4 (Doheny & Ganem, 1980). [K(18c6)]OAc (OAc = acetate) has been shown to be useful as an acetylation agent for alkyl halides (Liotta et al, 1974), and over the past few years 'CECILs' (crown ether complex cation ionic liquids) such as [K(18c6)]OAc and [K(18c6)]OH gained in importance as basic catalysts for various organic transformations (e.g.…”
Hydrogen bonding plays an important role in the structures of two solvated forms of [K(18c6)]OAc (18c6 = 18-crown-6 = 1,4,7,10,13,16-hexaoxacyclooctadecane and OAc = acetate).
“…Because of the short preparation time and simple product workup, many students will have the opportunity to complete this experiment in less than one laboratory session. If so, this work can be used as a complement to experiments on crown ethers described in THIS JOURNAL (5,8) or elsewhere (9).…”
“…• The oxidation of cyclohexene with KMnO 4 in benzene with either crown ether (18) or Aliquat 336 (19) as the LLPTcatalyst. It is found that the experimental procedure described in entry 5 can be used to oxidize cyclohexene.…”
Liquid–liquid phase transfer catalysis (LLPTC) plays an ever-increasing role in academic research and in the large scale industrial production of chemicals. This method involves a biphasic medium composed of water and an organic solvent in which the LLPT-catalyst plays a critical role in the transport of some water-soluble reagents (e.g., nucleophiles or bases) from water into the organic layer. This article provides a list of easy to perform and relatively safe experiments that may be used to demonstrate the extraction of some colorful water-soluble reagents by Aliquat 336 into ether. This demonstrative process serves to simulate the preliminary extractive step of an ionic species in LLPT-catalyzed reactions and introduce various undergraduate chemistry concepts and principles to students.
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