6533b7d6fe1ef96bd1266515

RESEARCH PRODUCT

STUDIES ON BICYCLO[3.3.1]NONANES FOR SYNTHESIS OF CYCLOOCTENES

Julio G. UronesAlicia JiménezIsidro S. MarcosHoward B. BroughtonPilar BasabeSonia G. San FelicianoNarciso M. GarridoMargarita ParraDavid Díez

subject

chemistry.chemical_compoundBicyclic moleculeChemistryStereochemistryOrganic ChemistryCrystal structureNmr dataCinnamaldehyde

description

This paper describes a full conformational and stereochemical study of bicylo[3.3.1]nonanes, obtained from the reaction between cinnamaldehyde and 1-morpholine 1-cyclohexene. NMR data and stereochemistry were unequivocally established and assigned by two-dimensional experiments and single-crystal X-ray analysis. The crystal structure of a minor compound, 4, is reported. Cyclooctenes, which are present in natural products with biological activities, were synthesized from the bicyclononanes via the Wharton fragmentation.

https://doi.org/10.1081/scc-120004065