Inhaltszusammenfassung

Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3-alkoxy-4-(p-chlorophenyl)-1,3-thiazole-2(3H)-thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the O-alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third...Synthetic, spectroscopic, and structural investigations provided evidence that distinguished neat 3-alkoxy-4-(p-chlorophenyl)-1,3-thiazole-2(3H)-thiones (CPTTORs), once developed to serve as alkoxyl radical precursors for storage and use on demand, showed background reactivity. Selectivity in these transformations was guided by the nature of the O-alkyl substituent. Two pathways reflected the inherent weakness of the N,O bond, leading to products of isomerization and rearrangement. In a third instance, methyl translocation from oxygen to sulfur occurred to furnish a heteroaromatic N-oxide at the expense of a cross conjugated pi-system. Consistent X-ray crystallographic data sets served as a basis for electronic structure method assessment in order to model aspects relevant to structure and decomposition chemistry that were not available from diffraction data. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) » weiterlesen» einklappen

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