Modified crown ether catalysts. 2. Synthesis of alkanoyl-, aroyl-, .alpha.-hydroxyalkyl- and alkylbenzo and alkylcyclohexano crown ethers

Stott, Paul E.; Bradshaw, Jerald S.; Parish, W. Wesley; Cooper, James W.

doi:10.1021/jo01311a033

Cited by 39 publications

(10 citation statements)

References 2 publications

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“…However in our system, it is easier to increase the lipophilicity of the carboxylic acid portion of the crown ether carboxylic acids. We now report results for competitive solvent extractions of alkali metals using the series of crown ether carboxylic acids 5-9 which possess a common dibenzo-16-crown-5 polyether ring system and carboxylic acid portions of varying lipophilicity (5)(6)(7)(8) or of a different spatial…”

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confidence: 99%

“…Reagents. Reaction of sym-hydroxydibenzo-16-crown-5 (6) with NaH in THF followed by the addition of the appropriate -bromocarboxylic acid produced 2-(sym-dibenzo-16-crown-5oxy)butanoic acid (5), 2-(sym-dibenzo-16-crown-5-oxy)hexanoic acid (6), 2-(sym-dibenzo-16-crown-5-oxy)octanoic acid (7), and 2-(sym-dibenzo-16-crown-5-oxy)decanoic acid (8) (7). The 5-(sym-dibenzo-16-crown-5-oxy)pentanoic acid (9) was synthesized by the reaction of sym-hydroxydibenzo-16-crown-5 (6) with NaH in THF followed by the addition of ethyl 5-bromovalerate (Aldrich, Milwaukee, WI).…”

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Solvent extraction of alkali metal cations from aqueous solutions by highly lipophilic crown ether carboxylic acids

Strzelbicki¹,

Bartsch²

1981

Anal. Chem.

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Solvent extraction of alkali metal cations from aqueous solutions by highly lipophilic crown ether carboxylic acids

Strzelbicki¹,

Bartsch²

1981

Anal. Chem.

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“…Although diheptanoyl-dibenzo-18-crown-6 (10) is relatively insoluble in most common organic solvents, diheptyl-dibenzo-18-crown-6 (11) is much more soluble in solvents such as chloroform, tetrahydrofuran, ethyl acetate and diethyl ether. Diheptanoyl-dibenzo-18-crown-6 (10) had been prepared previously by acylation with heptanoic acid and Eaton's reagent (phosphoric acid in methanesulfonic acid), but this method lead to both acylation and glycol cleavage products [17]. A Raney nickel reduction of the ketone in cyclohexanol was then used to prepare diheptyl-dibenzo-18-crown-6 (11).…”

Section: Synthesis Of Perfluoroalkylated Dibenzo-18-crown-6-ethersmentioning

confidence: 99%

Di(1H,1H,2H,2H-perfluorooctyl)-dibenzo-18-crown-6: A “light fluorous” recyclable phase transfer catalyst

Gourdet

Singh

Stuart

et al. 2010

Journal of Fluorine Chemistry

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“…23 The prod uct, alkyl (C18)-benzo-15-crown-5, was ob tained by the re ac tion be tween stearic acid (1.44 g) and mono-benzo-15-crown-5 (1.4 g) in 30 g of Eaton's re agent (40 mL methanesulfonic acid/6 g phos pho ric an hy dride) so lu tion at room tem per a ture for 6 hr and fol lowed by chlo ro form ex trac tion and recrystallization with haxanol. The fi nal prod uct of alkyl (C18)-benzo-15-crown-5 was iden ti fied us ing MS spec trum with M + = 534.4.…”

Section: Ex Per I Men Talmentioning

confidence: 99%

Piezoelectric Crystal Liquid Flow Detection Systems Based on Alkyl (C18)-Benzo-15-Crown 5 for Organic Compounds and Metal Ions

Sung

Shih

2005

Jnl Chinese Chemical Soc

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A wa ter in sol u ble long-chain crown ether alkyl (C18)-benzo-15-crown-5 was syn the sized and ap plied as a coat ing ma te rial on quartz crys tal mem branes of a liq uid flow pi ezo elec tric crys tal sen sor. The os cil lat ing crown ether-coated pi ezo elec tric (PZ) crys tal with a home-made com puter in ter face was pre pared as a liq uid chro mato graphic (LC) de tec tor for or ganic spe cies and metal ions in aque ous so lu tions. The os cil lat ing frequency of the quartz crys tal de creased due to the ad sorp tion of or ganic mol e cules or metal i ons on crown ether mol e cules. Ef fects of func tional group, mo lar mass, steric hin drance, and po lar ity of or ganic mol e cules on frequency re sponses of the crown ether coated PZ crys tal de tec tor were in ves ti gated. The fre quency re sponses of the crown ether coated PZ crys tal de tec tor for var i ous mol e cules were in the or der: amines > carboxylic ac ids > al co hols > ke tones. The crown ether PZ de tec tor also ex hib ited good sen si tiv ity for some heavy metal ions and the fre quency shifts were in the or der: Cr 3+ >> PbThe crown ether coated pi ezo elec tric crys tal LC de tec tor dem on strated low de tec tion lim its for var i ous po lar or ganic mol e cules, e.g., 6.0 × 10 -5 M for propylamine, and metal ions, e.g., 2.9 × 10 -5 M (1.8 ppm) for Cu 2+; the crown ether PZ de tec tor also gave good reproducibility when re used. A quite sen si tive elec tro chem i cal quartz crys tal microbalance (EQCM) de tec tion sys tem was also set-up for de tect ing trace heavy metal ions in so lu tions. The vari a tion in fre quency of the PZ crys tal and the dif fu sion cur rent were ob served si mul ta neously af ter the re duc tion in heavy metal ions such as Cu 2+ and Ni 2+ . The EQCM de tec tion sys tem ex hib ited fairly good sen si tiv ity, e.g., 112 Hz/ppm for Cu 2+ and a good de tec tion limit, e.g., 0.13 ppm for Cu 2+ ions. Com par i son be tween EQCM and PZ de tec tion sys tems was made and dis cussed.Key words: Crown ethers; Pi ezo elec tric liq uid chro mato graphic de tec tor; Or ganic mol e cules; Heavy metal ions; Elec tro chem i cal quartz crys tal microbalance. IN TRO DUC TIONPi ezo elec tric crys tals, e.g., quartz, BaTiO3, PZT (PbZrTiOx) and PLZT (PbLaZrOy), are well known to be sen si tive to pres sure on their sur face and have found widespread ap pli ca tions in com put ers, elec tronic equip ment, micro bal ances and com mu ni ca tion equip ment. The vi brational fre quency of an os cil lat ing pi ezo elec tric crys tal is decreased upon ad sorp tion of a for eign sub stance onto its surface. 1 The vari a tion in vi bra tional fre quency (∆F) re lated to the mass (Ms in g) of coat ing ma te ri als de pos ited on the crystal sur face of area A in cm2 and ba sic fre quency (Fo) of the pi ezo elec tric crys tal can be cal cu lated from Sauerbrey's equa tion [1]: ∆F = -2.3 × 10 6 × F o × (Ms/A). The the o ret i cal de tec tion limit of a 10 MHz os cil lat ing quartz crys tal can be es ti mated to be as small as 10 -12 g for...

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Modified crown ether catalysts. 2. Synthesis of alkanoyl-, aroyl-, .alpha.-hydroxyalkyl- and alkylbenzo and alkylcyclohexano crown ethers

Cited by 39 publications

References 2 publications

Solvent extraction of alkali metal cations from aqueous solutions by highly lipophilic crown ether carboxylic acids

Solvent extraction of alkali metal cations from aqueous solutions by highly lipophilic crown ether carboxylic acids

Di(1H,1H,2H,2H-perfluorooctyl)-dibenzo-18-crown-6: A “light fluorous” recyclable phase transfer catalyst

Piezoelectric Crystal Liquid Flow Detection Systems Based on Alkyl (C18)-Benzo-15-Crown 5 for Organic Compounds and Metal Ions

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