SYNTHESIS AND CHARACTERIZATION OF N-T-BOC PROTECTED PYRROLE-SULFUR OLIGOMERS AND POLYMERS

The synthesis and characterization of a new class of pyrrole-sulfur co mpounds is described. These compounds are designed to be precursors fo r an organic analogue of poly(sulfur nitride). Poly(N-t-BOC-2,5-pyrrol yl sulfide) was prepared from N-t-BOC-2,5-dibromopyrrole by first lith iating this compound with n-BuLi, followed by the addition of bis(p-to syl) sulfide. Similarly, bis(N-t-BOC-2-pyrrolyl) sulfide was prepared starting from N-t-BOC-2-bromopyrrole. Subsequent selective oxidation w ith one or two equivalents of m-CPBA quantitatively gave bis(N-t-BOC-2 -pyrrolyl) sulfoxide and -sulfone, respectively. Thermal deprotection of the t-BOC groups of the oligomers and the polymer resulted in decom position of these compounds; the latter is presumably due to a combina tion of sulfur-extrusion and polymerization.