Synthesis of new 10,11-dihydrodibenzo[a,d]cycloheptene S-thiocarbamate derivatives via a benzylic Newman-Kwart rearrangement

New S-thiocarbamates possessing a 10,11-dihydro-5H-dibenzo[a,d]cycloheptene moiety were obtained unexpectedly in the process of preparing new O-thiocarbamates starting from 5-dibenzosuberol (10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol) and aroyl-isothiocyanates. These compounds were obtained via a benzylic Newman-Kwart rearrangement mechanism. The structures of the new thiocarbamates were confirmed by elemental analysis, IR, and NMR spectroscopy and by X-ray crystallography.