Configuration and Conformation Study of S-Allyl O-Methyl N-(2- and 4-Substituted Acridin-9-yl)thiocarbonimidates in Relation to Their [3,3] Sigmatropic Rearrangement

Abstract

Configuration and conformations of S-allyl O-methyl N-(2- and 4-substituted acridin-9-yl)thiocarbonimidates were studied by means of NMR spectroscopy, dipole moments and quantum chemical calculations. The E configuration was proved for the unsubstituted and 2-chloro derivatives from the NOE-difference spectra. Experimental values of dipole moments were related to those obtained from vector addition. Quantum chemical calculations pointed to the chair conformation of these compounds in transition state for above-mentioned rearrangement.