60719-17-7Relevant academic research and scientific papers
Rearrangements of α-Diazo-β-hydroxyketones for the Synthesis of Bicyclo[m.n.1]alkanones
Li, Zhengning,Lam, Shuk Mei,Ip, Ignatius,Wong, Wing-Tak,Chiu, Pauline
supporting information, p. 4464 - 4467 (2017/09/11)
Rhodium-catalyzed decomposition of fused bicyclic α-diazo-β-hydroxyketones results in good yields of bridged bicyclo[m.n.1]ketones via a rearrangement pathway.
Construction of fused cyclooctanoid ring systems via seven-membered ring carbonyl ylides
Muthusamy, Sengodagounder,Babu, Srinivasarao Arulananda,Gunanathan, Chidambaram,Suresh, Eringathodi,Dastidar, Parthasarathi
, p. 801 - 811 (2007/10/03)
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.
