The insertion and extrusion of heterosulfur bridges. X. Conversions in the triphenylene‐triphenylo[4,5‐ bcd ] thiophene system | Zendy

Klemm L. H. | Zendy; Lawrence Ross F. | Zendy

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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.

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