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Review | Special issue | Vol 30, No. 2, 1990, pp.1219-1229
Published online, 1st January, 1970
DOI: 10.3987/REV-89-SR6
Interrelationships amongst peri-Condensed Thiophenes and Some Polycyclic Aromatics Hydrocarbons

LeRoy H. Klemm*

*Department of Chemistry, University of Oregon, Eugene, OR 97403, U.S.A.

Abstract

In the laboratory a peri-condensed thiophene (I) is commonly synthesized by inserting a sulfur bridging atom (from hydrogen sulfide or elemental sulfur) across the bay region of a polycyclic aromatic hydrocarbon precursor (II). This transformation may simulate the geochemical process whereby I forms in fossil fuels. Electrophilic substitution into I occurs ortho and/or para to the sulfur bridge and to the analogous positions in the isosteric hydrocarbon (III). The ultraviolet absorption spectra of I and III show similar shapes and characteristics. These interrelationships amongst I, II, and III are discussed.