THE SYNTHESIS AND NMR CHARACTERIZATION OF A SERIES OF 1,4-DIHYDRO-1,4-ETHANONAPHTALENE EPOXIDES

Article abstract of DOI:10.1016/S0040-4020(01)91908-8

A series of syn and anti epoxides derived from 5,8-disubstituted-1,4-dihydro-1,4-ethanonaphthalenes have been prepared.The role of the solvent on epoxidation stereochemistry has been explored.The structures of the epoxides were assigned with the aid of proton NMR coupled with chemical shift reagents.The C-13 spectra have also been assigned, and an unusual γ-effect of the epoxide structure noted.