Convenient synthesis of 1-thiohydroxypyrene by Newman-Kwart rearrangement

1-Thiohydroxypyrene( 1 ) and its two intermediates, 1-pyrenyl- O -thiocarbamate( 2 ) and 1-pyrenyl- S -thiocarbamate( 3 ), were synthesized using 1-hydroxypyrene as the starting material. The key synthetic step is Newman-Kwart rearrangement. The results indicate that the Newman-Kwart rearrangement is more effective in suitable solvent than conventional method based on pure organic compound. The structures of compounds 1 – 3 were characterized by FTIR, NMR, GC-MS and elementary analysis. The crystal structures of two new compounds( 2 and 3 ) were determined by single crystal X-ray diffraction analysis. The whole synthetic process is simple, mild and with high yield.