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Volumn , Issue 17, 2003, Pages 3412-3420

The effect of ring size on catenane synthesis

Author keywords

Catenanes; Macrocycles; Template synthesis

Indexed keywords

CARBONIC ACID; CATENANE; MACROCYCLIC COMPOUND; PHENOL DERIVATIVE; PRECATENANE; TOLANE; UNCLASSIFIED DRUG;

EID: 0041783889     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300232     Document Type: Article
Times cited : (25)

References (52)
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    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1619
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    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1212
  • 19
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    • D. A. Leigh, K. Moody, J. P. Smart, K. J. Watson, A. M. Z. Slawin, Angew. Chem. 1996, 108, 326; Angew. Chem. Int. Ed. Engl. 1996, 35, 306.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 306
  • 23
    • 0043232094 scopus 로고    scopus 로고
    • note
    • By application of the simple rule of arbitrary deformation for finding out whether two compounds are topological isomers (for a definition of topological isomerism see refs.[22,23]), the tether (i.e., the carbonate linkage) between the two rings of 7 and 8 can collapse to a point common to both rings. This converts 7 into 8 and vice versa. Therefore, within the strict definition of topology, 7 and 8 are topologically identical. However, the real molecules 7 and 8 cannot be converted into each other without bond breaking and this is strictly forbidden in topology. Because of this dilemma the term "residual topology" was recently suggested in ref.[21]
  • 28
    • 0043232092 scopus 로고    scopus 로고
    • note
    • 3N.
  • 30
    • 0042229854 scopus 로고    scopus 로고
    • note
    • α of 8c, 1c, and 2c, respectively). The data for the corresponding compounds with smaller rings are nearly the same.
  • 31
    • 0042730781 scopus 로고    scopus 로고
    • note
    • 1H NMR signals and FD-MS signals were found for products from experiments with ring precursor 5a(H) and a model compound for 5(H) bearing two methoxy groups instead of the long alkoxy substituents.
  • 33
    • 0042730785 scopus 로고    scopus 로고
    • note
    • 1H NMR signals are two broadened singlets at δ = 8.08 and 8.07 ppm and a triplet at δ = 2.93 ppm. This compound was eluted from silica gel only upon increasing the polarity of the solvent.
  • 34
    • 0043232091 scopus 로고    scopus 로고
    • note
    • 2 and finally distilled.
  • 35
    • 0043232090 scopus 로고    scopus 로고
    • note
    • The SEC traces of the mixtures of precatenanes 7 and dumb-bells 8 as obtained after column chromatography can be found in ref.[35]
  • 36
    • 0042730784 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopic data of 9b and 1b and of 10c and 11c, respectively.
  • 37
    • 0042730783 scopus 로고    scopus 로고
    • note
    • [35]) as an alternative structure for the isolated compounds was excluded for 9a, 9c, and 10c by a combination of SECs, mass spectrometry, and NMR spectroscopy, as described for 9b in ref.[18]
  • 40
    • 0042730786 scopus 로고    scopus 로고
    • note
    • A related result was reported by Isele et al. (refs. [4,381). In this case the size of the threaded ring was kept constant and the length of the threading ring precursor was varied.
  • 42
    • 0042229850 scopus 로고    scopus 로고
    • note
    • The formation of some catenane due to entanglement of the long chains is possible, but only with a very low probability.
  • 43
    • 0041729488 scopus 로고    scopus 로고
    • note
    • The activation energy for the oxidative alkyne dimerization is assumed to be the same for the conformers A, B, and C.
  • 44
    • 0042730782 scopus 로고    scopus 로고
    • note
    • α signals of 7 and 8 is small (Δδ = 0.01 or 0.02) the integration is not very precise. Nevertheless, the figures are sufficiently accurate clearly to show the trend that, the larger the rings, the more dumbbell is formed.
  • 46
    • 0041729489 scopus 로고    scopus 로고
    • note
    • in other strategies (see refs.[10-17]), the species with geometrically arranged catenane subunits are formed in situ and reversibly. The formation of non-entwined rings as side products of catenane formation is therefore not necessarily due to conformational changes as discussed here.
  • 48
    • 0041729490 scopus 로고    scopus 로고
    • note
    • 2 is its tendency to form emulsions with water. However emulsions can be avoided through addition of diethyl ether. This makes the extractive workup straightforward. To avoid hydrolysis of 2 when THF is used, either the THF must be removed or the reaction mixture must be diluted with a large amount of diethyl ether before water is added.
  • 49
    • 0042229852 scopus 로고    scopus 로고
    • note
    • The carbonate cleavage is very slow at room temperature, so cleavage at 50 °C, as described for the preparation of 9b, and 9c, is recommended.
  • 50
    • 0042229851 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of the crude products are shown in the Supporting Information.
  • 51
    • 0042730780 scopus 로고    scopus 로고
    • note
    • As described in ref.[18] 9b and 1b can be separated by chromatography.
  • 52
    • 0042229848 scopus 로고    scopus 로고
    • note
    • 3 (see NMR spectra of 2c, 10c, and 11c in the Supporting Information). We assume a structural defect associated with the dimethylphenol moiety.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.