Synthesis, NMR and molecular modeling studies on the stereochemistry of 2-aryl-3-(2 ',4 '-dinitrophenylthio)cyclohexenes

Ten 2-aryl-3-(2',4'-dinitrophenylthio)cyclohexanes were prepared, their H-1 NMR spectra measured and chemical shifts assigned on the basis of nuclear Overhauser enhancements, H,H-COSY spectra and other considerations. Analysi s of the data suggests the preference of the conformer with (i) the arylthi o group in the axial orientation and (ii) the dinitrophenyl group oriented away from the cyclohexene ring. The NOE results and molecular modeling calc ulations also support the above conclusions. Copyright (C) 2000 John Wiley & Sons, Ltd.