Studies on the synthesis and properties of open-chain and macrocyclic crown compounds

Si, Jiumin; Wu, Yangjie; Cai, Li‐Zhen; Liu, Yizhen; Du, Baoshi; Xu, Ting; An, Hongyu

doi:10.1007/bf00708784

Cited by 7 publications

(4 citation statements)

References 23 publications

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“…For related structures, see: Yu et al (2006); Ding et al (2007). For related literature, see: Si et al (1994).…”

Section: Related Literaturementioning

confidence: 99%

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{1,8-Bis[2-(2-oxidobenzylideneamino)phenoxy]-3,6-dioxaoctane}nitratopraseodymium(III) trichloromethane solvate

Liu¹,

Wang²,

Tang³

et al. 2008

Acta Cryst E

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In the title compound, [Pr(C32H30N2O6)(NO3)]·CHCl3, the PrIII ion is ten-coordinated by eight O atoms and two N atoms from the acyclic crown-type Schiff base ligand and the bidentate nitrate group. The coordination polyhedron around PrIII is a distorted bicapped square antiprism. The chloroform solvent molecule is not involved either in coordination to the PrIII center or in hydrogen bonding to the complex. The Pr—O(phenolate) bonds are significantly shorter than the Pr—O(ether) and Pr—O(nitrate) bonds, which suggests that the Pr—O(phenolate) bond is stronger than these other bonds. In the crystal structure, the acyclic crown-type Schiff base ligand wraps around the PrIII centre, forming a pseudo-ring.

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“…For related structures, see: Yu et al (2006); Ding et al (2007). For related literature, see: Si et al (1994).…”

Section: Related Literaturementioning

confidence: 99%

“…H 2 L was synthesized using a literature method (Si et al,1994). The title compound Pr(NO 3 )(C 32 H 30 O 6 N 2 )(CHCl 3 ) was synthesized as follows: NaOH (8.0 mg, 0.2 mmol) was added to 10 ml of ethyl acetate solution containing H 2 L (54.0 mg, 0.1 mmol).…”

Section: S2 Experimentalmentioning

confidence: 99%

{1,8-Bis[2-(2-oxidobenzylideneamino)phenoxy]-3,6-dioxaoctane}nitratopraseodymium(III) trichloromethane solvate

Liu¹,

Wang²,

Tang³

et al. 2008

Acta Cryst E

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“…In conjunction with the ongoing work in our laboratory on the synthesis and complex formation of macrocyclic compounds with different molecules, − we found that phenol-containing macrocyclic diamides efficiently catalyzed the addition of ammonium thiocyanate to epoxide to form β-hydroxy thiocyanate. Five new phenol-containing macrocyclic diamides as well as dibenzo-18-crown-6-, 18-crown-6-, benzo-15-crown-5-, and pyridine-containing macrocyclic diamide 19 were selected as catalysts in these reactions.…”

Section: Introductionmentioning

confidence: 99%

Phenol-Containing Macrocyclic Diamides as New Catalysts in the Highly Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates

2001

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The regioselective ring-opening reactions of some epoxides with ammonium thiocyanate in the presence of a series of new phenol-containing macrocyclic diamides and also dibenzo-18-crown-6-, 18-crown-6-, benzo-15-crown-5-, and pyridine-containing macrocyclic diamide have been studied. The epoxides were subject to cleavage by NH(4)SCN in the presence of these catalysts under mild reaction conditions in various aprotic solvents. In this study, reagents and conditions have been discovered with which the individual beta-hydroxy thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. The results can be discussed in terms of a four-step mechanism: (1) formation of complex between catalyst and NH(4)SCN, (2) release of SCN(-) nucleophile from the complex, (3) reaction of the active nucleophile at the less sterically hindered site in the epoxide, and (4) regeneration of catalyst. The major advantages of this method are as follows: (1) high regioselectivity, (2) simple regeneration of catalyst, (3) its reuse through several cycles without a decrease in activity, and (4) ease of workup of the reaction.

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“…In addition, the complexation and decomplexationofopen-chaincrownethersaregenerallyfaster thanthecorrespondingmacrocyclicpolyethers. 2 Therefore,they areexcellentreagentsforactivatingion-selectiveelectrodesand extractsofrareearthions. 3 A chemical diagram of the title complex is shown in Fig.…”

mentioning

confidence: 99%

Crystal Structure of [CeL(NO3)] CHCl3, H2L = 1,8-Bis[2-(2-hydroxyphenylideneimino)phenoxy]-3,6-dioxaoctane

et al. 2008

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Studies on the synthesis and properties of open-chain and macrocyclic crown compounds

Cited by 7 publications

References 23 publications

{1,8-Bis[2-(2-oxidobenzylideneamino)phenoxy]-3,6-dioxaoctane}nitratopraseodymium(III) trichloromethane solvate

{1,8-Bis[2-(2-oxidobenzylideneamino)phenoxy]-3,6-dioxaoctane}nitratopraseodymium(III) trichloromethane solvate

Phenol-Containing Macrocyclic Diamides as New Catalysts in the Highly Regioselective Conversion of Epoxides to β-Hydroxy Thiocyanates

Crystal Structure of [CeL(NO3)] CHCl3, H2L = 1,8-Bis[2-(2-hydroxyphenylideneimino)phenoxy]-3,6-dioxaoctane

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