New substituted dibenzothiophenes have been prepared and characterized. Selective functionalizations utilized substitutions of lithiodibenzothiophenes available from established methodology. New dibenzothiophenes prepared include 2‐(bromomethyl)dibenzothiophene (5), 2‐(thiomethyl)dibenzothiophene (6), 2‐S‐phenylthiomethyldibenzothiophene (24), 2‐S‐(2′‐dibenzothiophenylmethyl)thiomethyldibenzothiophene (25), 2‐S‐methyldibenzothiophene (30), 2‐S‐(p‐bromophenyl)dibenzothiophene (31), and 2‐S‐benzyldibenzothiophene (33). Dibenzothiophenes prepared from 4‐lithiodibenzothiophene include 4‐(bromomethyl)dibenzothiophene (13), 4‐(thiomethyl)dibenzothiophene (14), 4‐S‐(4′‐dibenzothiophenylmethyl)thiomethyldibenzothiophene (26), 4‐S‐(p‐tolyl)dibenzothiophene (34), 4‐S‐methyldibenzothiophene (35), 4‐S‐benzyldibenzothiophene (37), and 4‐S‐(p‐bromophenyl)dibenzothiophene (36). Similarly new 2,8‐disubstituted dibenzothiophenes prepared include 2,8‐bis(thiomethyl)dibenzothiophene (19), 2,8‐bis(S‐benzyl)dibenzothiophene (27), 2,8‐bis(S‐p‐tolyl)dibenzothiophene (28) and 2,8‐bis(S‐methyl)dibenzothiophene (29). The cmr chemical shift data for these dibenzothiophenes are also included.

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General Procedure for the Preparation of 4 and 7. To a stirred solution of methylenetriphenylphosphorane [prepared from methyltriphenylphosphonium bromide (5.71 g, 16 mmol) and n-BuLi (10.67 mL of 1.5 M hexane solution, 16 mmol) in THF under ice cooling] was added a solution of 3 (or 6) (13.6 mmol) in THF (30-60 mL) under ice cooling. The mixture was warmed

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In Gegenwart von Pyridinium‐tosylat (II) werden gemischte Acetale (I) in die symmetrischen Vertreter (III) und (IV) umgewandelt.