Resolution of trans-Cycloöctene; Confirmation of the Asymmetry of cis-trans-1,5-Cycloöctadiene

Cope, Arthur C.; Ganellin, C. Robin; Johnson, Harry W.

doi:10.1021/ja00875a036

Cited by 55 publications

(19 citation statements)

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“…Includes 2.2 % of a material which gives the same decomposition peaks on vpc analysis as does 1-phenylcyclooctanol. 6 Includes 0.5% of a methylphenylcycloheptene (see text).…”

mentioning

confidence: 99%

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹

Cope¹,

Kinnel²

1966

J. Am. Chem. Soc.

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“…Includes 2.2 % of a material which gives the same decomposition peaks on vpc analysis as does 1-phenylcyclooctanol. 6 Includes 0.5% of a methylphenylcycloheptene (see text).…”

mentioning

confidence: 99%

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹

Cope¹,

Kinnel²

1966

J. Am. Chem. Soc.

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“…The two enantiomers have been resolved by Cope and coworkers [115,116] who determined the absolute configuration of the enantiomers [117]; the (À)-enantiomer has been shown to be R and the (+)-enantiomer S. The molecule possesses C 2 point group, having only the C 2 axis passing through the center of the double bond and bisecting the 5-6 bond. In the higher homologues increase in the mobility of the polymethylene chain decreases the rotational barrier.…”

Section: R-( )-E-cyclooctene (7)mentioning

confidence: 99%

Fundamental Stereochemical Concepts and Nomenclatures

Talapatra

2014

Chemistry of Plant Natural Products

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“…Coordination chemistry provides another way of separating enantiomers, as shown by a method developed by Cope et al 18 The two enantiomers of trans-cyclooctene can be separated after being coordinated to Pt(0) in a square-planar complex in which one of the ligands is chiral and optically pure.…”

Section: Formation Of Diastereomeric Complexesmentioning

confidence: 99%

Resolution of topologically chiral molecular objects

Chambron¹,

Dietrich‐Buchecker²,

Rapenne³

et al. 1998

Chirality

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The enantiomers of topologically chiral molecular objects cannot be interconverted by a continuous deformation. It must be noted that this behavior is opposite to that of molecules showing classical or Euclidian chirality. Interlocked oriented rings and the trefoil knot are prototypical topologically chiral objects. We have been designing a transition-metal templated route to the corresponding real molecules (i.e., [2]-catenanes and molecular knots) using copper(I) as the template and 2,9-diphenyl-1,10-phenanthroline (dpp) based ligands. The precursor to the catenane species was a tetrahedral Cu(dpp) 2 + complex in which the two ligands fit in around Cu(I), thereby allowing the interlocking process. In the case of the knot, the precursor was a double-stranded helical complex in which two bis-phenanthroline ligands wrap around two Cu(I) ions. The compounds were obtained as racemates and were resolved as their Cu(I) complexes either by HPLC on chiral stationary phases or by diastereoselective crystallization. For the trefoil knot (K ⅐ 2Cu + ), the latter method proved to be the most efficient. It took advantage of the dicationic nature of the species to be resolved.

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Resolution of trans-Cycloöctene; Confirmation of the Asymmetry of cis-trans-1,5-Cycloöctadiene

Cited by 55 publications

References 0 publications

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹

Fundamental Stereochemical Concepts and Nomenclatures

Resolution of topologically chiral molecular objects

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Resolution of trans-Cycloöctene; Confirmation of the Asymmetry of cis-trans-1,5-Cycloöctadiene

Cited by 55 publications

References 0 publications

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d5 Tosylates1

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d5 Tosylates1

Fundamental Stereochemical Concepts and Nomenclatures

Resolution of topologically chiral molecular objects

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Product

Resources

About

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹

Proximity Effects. XLIV. Stereospecific Synthesis and Solvolysis of cis- and trans-5-Phenylcyclooctyl and cis- and trans-5-Phenylcyclooctyl-1,2,2,8,8-d₅ Tosylates¹