Synthesis and characterization of N-t-BOC protected pyrrole-sulfur oligomers and polymers

L. Groenendaal, K. Pieterse, J.A.J.M. Vekemans, E.W. Meijer

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The synthesis and characterization of a new class of pyrrole-sulfur compounds is described. These compounds are designed to be precursors for an organic analogue of poly(sulfur nitride). Poly(N-t-BOC-2.5-pyrrolyl sulfide) was prepared from N-t-BOC-2,5-dibromopyrrole by first lithiating this compound with n-BuLi, followed by the addition of bis(p-tosyl) sulfide. Similarly, bis(N-t-BOC-2-pyrrolyl) sulfide was prepared starting from N-t-BOC-2-bromopyrrole. Subsequent selective oxidation with 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 decomposition of these compounds; the lauer is presumably due to a combination of sulfur-extrusion and polymerization.
Original languageEnglish
Pages (from-to)257-266
Number of pages10
JournalSynthetic Communications
Issue number2
Publication statusPublished - 1997


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