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Synthesis of multisulfur‐containing substituted dibenzothiophenes
Author(s) -
Dunkerton L. V.,
Barot B. C.,
Nigam A.
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240341
Subject(s) - dibenzothiophene , chemistry , organic chemistry , sulfur
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.