Synthesis of multisulfur‐containing substituted dibenzothiophenes

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Abstract
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.