Nuclear magnetic resonance spectra and structure of fluorinated oxetanes

Fluorine, hydrogen, and carbon-13 nuclear magnetic resonance spectral data are reported for a variety of oxetane compounds containing fluorine on or near the ring. Effects of substituents on the spectra are analyzed and correlations of chemical shifts and coupling constants in terms of molecular structure are presented. Application of NMR permits the assignment of the regiochemistry and stereochemistry of the products of photochemical reactions between carbonyl compounds and olefins. Steric interactions and possible deviations from ring planarity are discussed in relation to the pathways of nuclear spin–spin interaction and to the trends observed in NMR parameters.