Reaction of cyclo-octa-1,5-diene with phenyl selenocyanate in alcohol or aqueous tetrahydrofuran in the presence of copper(II) chloride produces an isomeric mixture of 2,6-bis(phenylseleno)-9-oxabicyclo[3.3.1]-nonane and 2,5-bis(phenylseleno)-9-oxabicyclo[4.2.1]nonane in good yield, the isomer ratio being solvent dependent.
S. Uemura, A. Toshimitsu, T. Aoai and M. Okano, J. Chem. Soc., Chem. Commun., 1979, 610 DOI: 10.1039/C39790000610
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