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Abstract:
Reaction of the trilithium salt, prepared by treatment of 1,1,1-tris(2-bromo-5-methyl-3-thienyl)ethane, with O,O′-diethyl thiocarbonate gave thiophenetriptycene-8-thiol in 42% yield. The thiol was not oxidized with m-chloroperoxybenzoic acid (MCPBA). However, treatment of the thiol with NaH in THF followed by oxidation with MCPBA gave thiophenetriptycene-8-sulfenic acid in 70% yield. The structure of the sulfenic acid was determined by spectroscopic means and X-ray single-crystal analysis.
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