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The insertion and extrusion of heterosulfur bridges. X. Conversions in the triphenylene‐triphenylo[4,5‐ bcd ] thiophene system
Author(s) -
Klemm L. H.,
Lawrence Ross F.
Publication year - 1979
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.5570160340
Subject(s) - triphenylene , chemistry , thiophene , sulfur , sulfoxide , mesitylene , sulfide , sulfone , methanol , photochemistry , yield (engineering) , hydrogen sulfide , monoxide , catalysis , medicinal chemistry , organic chemistry , molecule , materials science , metallurgy
Sulfur bridging of triphenylene ( 3 ) to form triphenylo[4,5‐ bcd ]thiophene ( 4 ) is effected in 18% yield by means of hydrogen sulfide and a molybdena catalyst (CMA‐1) at 500°. Compound 4 is purified through its sulfoxide, converted into its sulfone ( 6 ), and desulfurized (by means of CMA‐1 plus methanol‐benzene) back to 3 . The ultraviolet absorption spectrum of 4 resembles closely that of benzo[e]pyrene. On electron impact 4 shows little skeletal fragmentation, while 6 readily evolves sulfur monoxide and the formyl group.