Preparation of New Nitrogen-Bridged Heterocycles 67. Syntheses of α,α′-Bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene Derivatives and Their Conformational Structures

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The alkaline treatment and dehydrogenation of pyridinium salts, formed from the S-alkylations of 3-(1-pyridinio)thiophene-2-thiolates with α,α-dibromo-o-, m-, or p-xylene, provided the corresponding α,α′-bis[(thieno[3,4-b]indolizin-3-yl)thio]-o-, m-, and p-xylene derivatives in low to good yields. Both 1H-NMR and UV–Vis spectra of these products supported distinctly the predominance of the gauche–gauche conformation in relation to the two sulfide linkages as the spacer in these molecules. On the other hand, the X-ray analyses indicated the expected gauche–gauche conformation for the m- and the p-xylene derivatives, but the anti–anti one for the o-xylene derivative.