Reaction of cyclic epoxide compounds with triphenylphosphine

Significant differences were found in the reactivity of a series of epoxides of cycloalkenes and methylenecycloalkanes and diepoxides in reaction with triphenylphosphine, depending both on the steric effects of the cyclic fragments and on their strain. The level of the strain can be judged indirectly from the chemical shifts of the /sup 1/H and /sup 13/C nuclei and the spin-spin coupling constants of the C-H bonds in the epoxide ring.