Structure of 5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine (Tröger's base) at 163 K

Larson, S. B.; Wilcox, Craig S.

doi:10.1107/s0108270186096713

Cited by 46 publications

(34 citation statements)

References 7 publications

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“…Next, XRD analysis of the precipitated racemic and enantiopure crystals was carried out. The crystal morphology of the racemic compound was found to correspond to that of the orthorhombic structure (space group Pccn, with Z 12) reported previously [20]. The crystal structure of the pure enantiomer, which has not been reported in the literature before, was determined to be orthorhombic as well.…”

mentioning

confidence: 54%

Solid‐Liquid Equilibrium of Tröger's Base Enantiomers in Ethanol: Experiments and Modelling

Worlitschek

Bosco

Huber

et al. 2004

Helvetica Chimica Acta

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Thermodynamic properties of the enantiomers of the Trˆger×s base as crystals and in ethanol solutions have been studied by means of a suite of analytical techniques. We report the melting diagrams of the two enantiomers, providing evidence for the formation of a solid racemic compound. We present also ternary equilibrium data about the solubility of the two enantiomers in ethanol at 258, 358, and 508. The melting-diagram data are described well by the SchroederÀVan Laar and PrigogineÀVieland equations, when the melting temperatures and enthalpies of pure enantiomer and of the racemic compound are provided and with the assumption that the melting behavior is ideal. The ternary equilibrium data were well-described when nonideality of mixtures of ethanol and the enantiomers is accounted for in terms of the non-random two liquids (NRTL) model. Finally, we present the newly determined X-ray crystal structure of an orthorhombic form of the pure Trˆger×s base ()-enantiomer.

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confidence: 54%

Solid‐Liquid Equilibrium of Tröger's Base Enantiomers in Ethanol: Experiments and Modelling

Worlitschek

Bosco

Huber

et al. 2004

Helvetica Chimica Acta

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“…The dihedral angle at the base of 21 is 93.7 o , similar to the angle present in Tröger's base 1, where the aromatic rings in the two types of molecule present in the unit cell give rise to dihedral angles of 92.9° and 97.4°. 44 The similarity of these values suggests that the presence of the phenyl ring above the cavity in the substituted methano-strapped compounds is unlikely to impart a significant influence on the geometry of the base of the compounds. …”

mentioning

confidence: 81%

Synthesis of 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and a demonstration of their reactivity to afford methano strap-modified Tröger’s base analogues

Mahon¹,

Craig²,

Try³

2008

Arkivoc

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Tröger's base analogues are of interest in areas such as host-guest chemistry, synthetic receptor design and asymmetric catalysis. We foresee that access to diverse functionality attached to the bridge of Tröger's base compounds will be beneficial for the development of these applications. As a starting point, we report a facile and general methodology to prepare a range of diversely functionalised 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines, compounds that may be viewed as "strap-clipped" Tröger's bases. As a demonstration of their reactivity, these compounds were reacted with benzaldehyde to introduce phenyl substituted straps onto a Tröger's base framework.

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“…It features a central bicyclic aliphatic unit fused with the two benzene rings. Curiously, only in 1986, this structure was unambiguously confirmed with the aid of single-crystal X-ray-diffraction (XRD) analysis [4] -a surprisingly long gap for an air-stable, soluble, very easily available compound with a molecular weight of only 250. The two tertiary bridgehead N-atoms of this C 2 -symmetrical molecule are stereogenic centers.…”

mentioning

confidence: 86%

“…5). Interestingly, addition of NH 4 Cl to the reaction mixture during the synthesis of 29 resulted in the increase of the ratio of cleft-shaped syn,syn and anti,syn isomers to the anti-anti isomer, suggesting a template effect of NH It is worth mentioning that Cl-atoms primarily served to block one of the orthopositions and, therefore, to exclude formation of other possible regioisomers. However, it turned out that these substituents also bring configurational stability: little or no interconversion was observed for all three diastereoisomers of 29 upon treatment with 3m HCl at temperatures up to 958 for 6 days.…”

Section: Synthesis Of Linear Tris-trçgers Base 29mentioning

confidence: 98%

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

Sergeyev

2009

Helvetica Chimica Acta

132

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Trçgers base is a well-known chiral molecule with a few unusual structural features. The chemistry of Trçgers base analogues has been greatly developed over the last 20 years, and numerous interesting applications in supramolecular chemistry and in molecular recognition have emerged. This Review gives a short overview of the chemistry of Trçgers base and its analogues, with particular focus on recent achievements in synthesis, enantiomer separations, and applications.

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Structure of 5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine (Tröger's base) at 163 K

Cited by 46 publications

References 7 publications

Solid‐Liquid Equilibrium of Tröger's Base Enantiomers in Ethanol: Experiments and Modelling

Solid‐Liquid Equilibrium of Tröger's Base Enantiomers in Ethanol: Experiments and Modelling

Synthesis of 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines and a demonstration of their reactivity to afford methano strap-modified Tröger’s base analogues

Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base Analogues

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