Synthesis and NMR spectra of the syn and anti isomers of substituted cyclobutanes-evidence for steric and spatial hyperconjugative interactions

Abstract

The syn and anti isomers of cis,cis-tricyclo[5.3.0.02,6]dec-3- ene derivatives have been synthesized and their 1H and 13C NMR spectra unequivocally analyzed. Both their structures and their 1H and 13C NMR chemical shifts were calculated by DFT, the latter two calculations employing the GIAO perturbation method. Additionally, calculated NMR shielding values were partitioned into Lewis and non-Lewis contributions from the bonds and lone pairs involved in the molecules by accompanying NBO and NCS analyses. The differences between the syn and anti isomers were evaluated with respect to steric and spatial hyperconjugation interactions. © 2011 Elsevier Ltd. All rights reserved.