Collect. Czech. Chem. Commun. 1998, 63, 387-393

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

Ivan Danihela, Kalevi Pihlajab, Ján Imricha, Gejza Suchára, Pavol Kristiana, Stanislav Böhmc and Slávka Hočováa

a Department of Organic Chemistry, Faculty of Sciences, P.J. Šafárik University, Moyzesova 11, SK-04167 Košice, Slovak Republic
b Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
c Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


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.

Keywords: Acridines; Thiocarbonimidates; NOE NMR spectroscopy; Dipole moments; PM3 and HF/3-21G calculations.