Construction of fused cyclooctanoid ring systems via seven-membered ring carbonyl ylides

Muthusamy, Sengodagounder ; Babu, Srinivasarao Arulananda ; Gunanathan, Chidambaram ; Suresh, Eringathodi ; Dastidar, Parthasarathi (2002) Construction of fused cyclooctanoid ring systems via seven-membered ring carbonyl ylides Bulletin of the Chemical Society of Japan, 75 (4). pp. 801-811. ISSN 0009-2673

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A series of α-diazo carbonyl compounds tethered to cyclopentanone/cyclohexanone/1-tetralone units have been synthesized using a diazomethane solution to construct various fused cyclooctane ring systems via rhodium-generated carbonyl ylides. The reaction of rhodium(II) acetate dimer with various α-diazo carbonyl compounds generated transient cyclic seven-membered ring carbonyl ylides, which underwent facile 1,3-dipolar cycloadditions with dipolarophiles, like N-phenylmaleimide, p-benzoquinone, and DMAD to furnish a variety of fused epoxy-bridged cyclooctane ring systems in a tandem manner. Interestingly, an oxepine ring system was generated via an intramolecular proton transfer of a seven-membered ring carbonyl ylide. A tri-oxa polycyclic compound was obtained in the case of p-benzoquinone as dipolarophile. A single-crystal X-ray analysis of a fused cyclootanoid derivative is reported to decisively establish the structure and stereochemistry of the fused epoxy-bridged cyclooctane ring systems; a further analysis revealed the existence of a unique intermolecular C–H···π interaction motif in the solid-state architecture.

Item Type:Article
Source:Copyright of this article belongs to Chemical Society of Japan.
ID Code:112836
Deposited On:19 Apr 2018 11:40
Last Modified:19 Apr 2018 11:40

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