Chemistry:Dibenzothiophene
Dibenzothiophene (DBT, diphenylene sulfide) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It has the chemical formula C12H8S. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its disubstituted derivative 4,6-dimethyldibenzothiophene are problematic impurities in petroleum.[1]
Synthesis and reactions
Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride.[2]
Reduction with lithium results in scission of one C-S bond. With butyllithium, this heterocycle undergoes stepwise lithiation at the 4-position. S-oxidation with peroxides gives the sulfoxide.[3]
Dibenzothiophene is electron-rich, and naturally undergoes aromatic substitution para to the sulfide. Oxidation to the sulfoxide or sulfone leaves the compound electron poor, and substitution occurs at the meta position instead.[4]
References
- ↑ Ho, Teh C. (2004). "Deep HDS of Diesel Fuel: Chemistry and Catalysis". Catalysis Today 98 (1–2): 3–18. doi:10.1016/j.cattod.2004.07.048.
- ↑ Klemm, L. H.; Karchesy, Joseph J. (1978). "The Insertion and Extrusion of Heterosulfur Bridges. VIII. Dibenzothiophene from Biphenyl and Derivatives". Journal of Heterocyclic Chemistry 15 (4): 561–563. doi:10.1002/jhet.5570150407.
- ↑ Waldecker, Bernd; Kafuta, Kevin; Alcarazo, Manuel (2019). "Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate". Organic Syntheses 96: 258–276. doi:10.15227/orgsyn.096.0258.
- ↑ Bhanuchandra, M.; Yorimitsu Hideki. "Encyclopedia of Reagents for Organic Synthesis". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.
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