Chemistry of the Phenoxathiins VII. A Re-Examination of the Mauthner Systhesis of 1,3-Dinitrophenoxathiin for the Possible Occurrence of a Smiles Rearrangement

Abstract

Abstract The preparation of 1,3-dinitrophenoxathiin represents the first reported synthesis of the phenoxathiin ring system. Based on known relative nucleophilicities either an unprecedented reversal of nucleophilicities or the occurrence of a Smiles Rearrangement would be required to account for the reported substituent locations. The re-examination of this synthesis with confirmation of actual substituent locations by 13C-nmr and the correction of the original literature is described.