Synthese mittlerer und großer Ringe, XXVIII. Die Rutheniumtetroxid‐Oxidation von 3,6‐Alkano‐4,5‐oligomethylenoxepinen Ein neuer Weg zu makrocyclischen Di‐, Tri‐ und Tetraketonen

Synthesis of Medium and Large Rings, XXXII']. -The [6](3,6)0xepinophane-[6](2,J)Furanophane Ring Contraction with Ruthenium TetroxideA one-pot synthesis of the furanophanes 2a and 2b by ring [7](3,6)oxepinophane l c leads to a complex mixture of the contraction of the oxepinophanes l a and l b is described. Ev-products 2d and 6 -10. 2a undergoes Diels-Alder reactions idence is presented that the reaction proceeds by subsequent with benzyne and 2,3-naphthalyne to give 11 and 12. The latter oxidation of two double bonds via the intermediates 3 and 4. forms the stable iron tricarbonyl complex 13. The structures On treatment with hydrochloric acid cis-4 gives 2a by 1,4-of 2c, 4,10,11, and 13 have been established by X-ray analyses. Die Konstitutionen 2a und 2b wurden vor allem durch Vergleich der 13C-NMR-und UV-Spektren rnit denen der Furan-3,4-dicarbon~aure~~**~~ nahegelegt und schlieBlich durch die Rontgenstrukturanalyse des aus 2 b und Diazomethan erhaltenen Dimethylesters 2c bewiesen (Abb. 1).2c wurde zunachst in der zentrosymmetrischen Raumgruppe P2,/n verfeinert ( R = 0.105). Hier fiihrte die starke Anisotropie der Schwingungsellipsoide zu einem Split-Mo-

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ChemInform Abstract: Synthesis of Medium and Large Rings. Part 28. The Ruthenium Tetroxide Oxidation of 3,6‐Alkano‐4,5‐oligomethyleneoxepins ‐ A New Approach to Macrocyclic Di‐, Tri‐, and Tetraketones.

Tochtermann¹,

Dibbern²,

Haase³

et al. 1991

ChemInform

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Synthese mittlerer und großer Ringe, XXVIII. Die Rutheniumtetroxid‐Oxidation von 3,6‐Alkano‐4,5‐oligomethylenoxepinen Ein neuer Weg zu makrocyclischen Di‐, Tri‐ und Tetraketonen

Cited by 4 publications

References 34 publications

Synthese mittlerer und großer Ringe, XXIX. Oxidation von 3,4‐Hexamethylenfuran zu 2,9‐Dioxodecan‐10‐olid

Synthese mittlerer und großer Ringe, XXIX. Oxidation von 3,4‐Hexamethylenfuran zu 2,9‐Dioxodecan‐10‐olid

Synthese mittlerer und großer Ringe, XXXI^[1] Die [6](3,6)Oxepinophan‐[6](2,5)Furanophan‐Ringverengung mit Rutheniumtetroxid

ChemInform Abstract: Synthesis of Medium and Large Rings. Part 28. The Ruthenium Tetroxide Oxidation of 3,6‐Alkano‐4,5‐oligomethyleneoxepins ‐ A New Approach to Macrocyclic Di‐, Tri‐, and Tetraketones.

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Synthese mittlerer und großer Ringe, XXVIII. Die Rutheniumtetroxid‐Oxidation von 3,6‐Alkano‐4,5‐oligomethylenoxepinen Ein neuer Weg zu makrocyclischen Di‐, Tri‐ und Tetraketonen

Cited by 4 publications

References 34 publications

Synthese mittlerer und großer Ringe, XXIX. Oxidation von 3,4‐Hexamethylenfuran zu 2,9‐Dioxodecan‐10‐olid

Synthese mittlerer und großer Ringe, XXIX. Oxidation von 3,4‐Hexamethylenfuran zu 2,9‐Dioxodecan‐10‐olid

Synthese mittlerer und großer Ringe, XXXI[1] Die [6](3,6)Oxepinophan‐[6](2,5)Furanophan‐Ringverengung mit Rutheniumtetroxid

ChemInform Abstract: Synthesis of Medium and Large Rings. Part 28. The Ruthenium Tetroxide Oxidation of 3,6‐Alkano‐4,5‐oligomethyleneoxepins ‐ A New Approach to Macrocyclic Di‐, Tri‐, and Tetraketones.

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Synthese mittlerer und großer Ringe, XXXI^[1] Die [6](3,6)Oxepinophan‐[6](2,5)Furanophan‐Ringverengung mit Rutheniumtetroxid