Preparation and structural characterization of a new class of stable thioketones:: ortho-hydroxythioacetophenones

ortho-Hydroxythioacetophenone and four structurally related ortho-hydroxyaryl methyl thioketones have been prepared from the corresponding ketones by reaction with gaseous H2S and HCl in ethanol under strictly controlled reaction conditions. The remarkable stability of the new monomeric thioketones seems to be due to a strong intramolecular O-H center dot center dot center dot S=C hydrogen bonding. (c) 2006 Elsevier Ltd. All rights reserved.