Abstract

2,4,6-Trithiaheptane (1a) has been prepared by lithium tetrahydridoaluminate reduction of the methiodide of 1,3,5-trithiane (2). Treatment of 1a with strong bases permitted formation of 3-alkylated derivatives (3) which could in turn be converted into diastereomeric mixtures of 3,5-dialkyl derivatives (4). A two-step alkylation of 1a with 1-bromo-3-chloropropane led to the formation of 2,6-bis(methylthio)thiane (5). Proton and 13C nmr spectral studies on these compounds, including the measurement of long-range carbon–proton coupling constants, are described; their mass spectra showed elimination of methanethiol as a characteristic major fragmentation pathway.

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