Bimolecular cycloadditions of nitrones to cyclic dienes, followed by MCPBA N-oxidations of the resulting unsaturated isoxazolidines, intramolecular cycloadditions of the derived nitrones, and hydrogenolyses of the corresponding tricyclic isoxazolidines, annelated the dienes to amino-and azabicyclic diols. Cycloocta-1,5-diene and IV-methylnitrone gave 3-azabicyclo[4.3.2]undecane-6,9-diol (1), 3-isopropyl-3-azabicyclo[3.3.3]undecane-6,9-diol (2), and 9-methylaminobicyclo[4.2.1]nonane-2,5-diol (4). jV-Phenylnitrone changed 1,5-cyclooctadiene to 9-(cyclohexylamino)bicyclo[4.2.1]nonane-2,5-diol (5). IV-Methylnitrone annelated 1,4-and 1,3-cyclohexadienes to 3-azabicyclo[3.3.1]nonane-6,8-and -6,9-diols (6 and 7, respectively). and 13C NMR spectroscopy established the regio-and stereoisomeric structures of the diols 1-6 and 20-21. Dynamic 13C NMR experiments showed that 2 and 3 took part in degenerate conformational equilibria like manxane. At about 65 °C proton-decoupled 13C NMR spectra of 2 and 3 showed eight and ten resonances, respectively. The number of resonances increased 10 (Scheme ). Adduct 25 was the only product we could
Aus 1,5‐Cyclooctadien (I) entstehen mit den NitTOHGH (H) die Addukte (III), mit den Cyclohexadienen (IV) und (VI) werden analoge Addukte (V) bzw. (VII) gebildet.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.