Polyenyl-substituted furans and thiophenes. A study of the electronic spectra—I

Reijendam, J. W. Van; Heeres, G. J.; Janssen, M. J.

doi:10.1016/s0040-4020(01)92999-0

Cited by 49 publications

(11 citation statements)

References 37 publications

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“…Clipping of isophthalaldehyde 64 occurs at an intermediate rate. This reactivity scale is consistent [183][184][185][186][187][188][189][190][191][192][193][194][195] with the electrophilicities of the different formyl groups.As expected, the dialdehyde 57 exhibits the most electrophilic behavior, while 65 exhibits the least. The donor-acceptor nature of the dumbbell-shaped dialkylammonium ion also affects the rates of clipping.…”

Section: Ammonium Ion Templated Synthesessupporting

confidence: 55%

“…In particular, the donor-acceptor nature of the terminal benzyl stoppering groups of the dumbbell-shaped dialkylammonium ions is varied from the p-electron-rich 60-H·PF 6 [189] through the p-electron-neutral 66-H·PF 6 to the p-electron-deficient 67-H·PF 6 . The dialdehyde is varied between 2,6-diformylpyridine 57 [190], isophthalaldehyde 64 and 2,5-diformylfuran 65 [191]. The tetraethylene glycol bis(2-aminophenyl)ether 58 is used as the diamine monomer in all the cases.…”

Section: Ammonium Ion Templated Synthesesmentioning

confidence: 99%

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Templated Synthesis of Interlocked Molecules

Aricò

Badjić

Cantrill

et al. 2005

Topics in Current Chemistry

195

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Section: Ammonium Ion Templated Synthesessupporting

confidence: 55%

Section: Ammonium Ion Templated Synthesesmentioning

confidence: 99%

Templated Synthesis of Interlocked Molecules

Aricò

Badjić

Cantrill

et al. 2005

Topics in Current Chemistry

195

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“…The nature of the terminal benzyl stoppering groups of the dumbbell‐shaped dialkylammonium ions was varied from π‐electron‐rich ( D OMe )14 through π‐electron‐neutral ( D Me ) to π‐electron‐deficient ( D

_{CF_{3}}

). The dialdehyde was varied from 2,6‐diformylpyridine ( P )15 via isophthalaldehyde ( B ) to 2,5‐diformylfuran ( F )16. We chose to keep the nature of the diamine, the tetraethylene glycol bis(2‐aminophenyl)ether A ,17 the same in all cases.…”

Section: Resultsmentioning

confidence: 99%

Kinetic versus Thermodynamic Control During the Formation of [2]Rotaxanes by a Dynamic Template‐Directed Clipping Process

Horn¹,

Ihringer²,

Glink³

2003

Chemistry A European J

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A template-directed dynamic clipping procedure has generated a library of nine [2]rotaxanes that have been formed from three dialkylammonium salts-acting as the dumbbell-shaped components-and three dynamic, imino bond-containing, [24]crown-8-like macrocycles-acting as the ring-shaped components-which are themselves assembled from three dialdehydes and one diamine. The rates of formation of these [2]rotaxanes differ dramatically, from minutes to days depending on the choice of dialkylammonium ion and dialdehyde, as do their thermodynamic stabilities. Generally, [2]rotaxanes formed by using 2,6-diformylpyridine as the dialdehyde component, or bis(3,5-bis(trifluoromethyl)benzyl)ammonium hexafluorophosphate as the dumbbell-shaped component, assembled the most rapidly. Those rotaxanes containing this particular electron-deficient dumbbell-shaped unit, or 2,5-diformylfuran units in the macroring, were the most stable thermodynamically. The relative thermodynamic stabilities of all nine of the [2]rotaxanes were determined by competition experiments that were monitored by (1)H NMR spectroscopy.

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“…5-Methylfurfural 17 was obtained from both the chloro and bromo derivative, when the reaction was catalysed by tin (II) chloride 10 or by zinc powder and acetic acid. 97 reported that the reaction of HMF with lead tetracetate in pyridine gave the dialdehyde in 37% yield. Morikawa 26,98,99 oxidised HMF with a variety of oxidants, for example chromium trioxide in pyridine, acetic anhydride in DMSO (Swern oxidation).…”

Section: Methodsmentioning

confidence: 99%