Tetrahydrothiophene

Tetrahydrothiophene is prepared by the reaction of tetrahydrofuran with hydrogen sulfide. This vapor-phase reaction is catalyzed by alumina and other heterogenous acid catalysts.Loev, B; Massengale, JT U. S. Patent 2,899,444, "Synthesis of Tetrahydrothiophene", 8/11/1959{{Ullmann|author=Jonathan Swanston|title=Thiophene|year=2006|doi=10.1002/14356007.a26_793.pub2}}

This compound is a ligand in coordination chemistry, an example being the complex chloro(tetrahydrothiophene)gold(I).{{cite book|vauthors = Uson R, Laguna A, Laguna M, Briggs DA, Murray HH, Fackler JP|author6-link=John P. Fackler Jr.|title=Inorganic Syntheses|chapter=(Tetrahydrothiophene)Gold(I) or Gold(III) Complexes|year=2007|volume=26 |pages=85–91|issn=1934-4716|doi=10.1002/9780470132579.ch17|isbn=9780470132579}}

Oxidation of THT gives the sulfone sulfolane, which is of interest as a polar, odorless solvent:

:{{chem2|C4H8S + 2 O -> C4H8SO2}}

Sulfolane is, however, more conventionally prepared from butadiene.

Both unsubstituted and substituted tetrahydrothiophenes are reported to occur in nature. For example, tetrahydrothiophene occurs as a volatile from Eruca sativa Mill. (salad rocket){{cite journal|last=Aissani|first=N|year=2006|title=Nematicidal Activity of the Volatilome of Eruca sativa on Meloidogyne incognita|journal=Journal of Agricultural and Food Chemistry|volume=63|issue=27|pages=6120–6125|doi=10.1021/acs.jafc.5b02425|pmid=26082278|display-authors=etal }} while monocyclic substituted tetrahydrothiophenes have been isolated from Allium fistulosum 'Kujou',{{cite journal|last=Fukaya|first=M|year=2018|title=Rare Sulfur-Containing Compounds, Kujounins A1 and A2 and Allium Sulfoxide A1, from Allium fistulosum 'Kujou'|journal=Organic Letters|volume=20|issue=1|pages=28–31|doi=10.1021/acs.orglett.7b03234|pmid=29227665|display-authors=etal}} Allium sativum (garlic),{{cite journal |last=Block |first=E |display-authors=etal |year=2018 |title=Ajothiolanes: 3,4-Dimethylthiolane Natural Products from Garlic (Allium sativum). |url=https://www.osti.gov/servlets/purl/1490686 |journal=Journal of Agricultural and Food Chemistry |volume=66 |issue=39 |pages=10193–10204 |doi=10.1021/acs.jafc.8b03638 |osti=1490686 |pmid=30196701 |bibcode=2018JAFC...6610193B |s2cid=52178061}} Allium cepa (onion),{{cite journal|last=Aoyagi|first=M|year=2011|title=Structure and Bioactivity of Thiosulfinates Resulting from Suppression of Lachrymatory Factor Synthase in Onion|journal=Journal of Agricultural and Food Chemistry|volume=59|issue=20|pages=10893–10900|doi=10.1021/jf202446q|pmid=21905712|bibcode=2011JAFC...5910893A|display-authors=etal}} Allium schoenoprasum (chives),{{cite journal|last=Fukaya|first=M|year=2019|title=Cyclic Sulfur Metabolites from Allium schoenoprasum var. foliosum|journal=Phytochemistry Letters|volume=29|pages=125–128|doi=10.1016/j.phytol.2018.11.018|bibcode=2019PChL...29..125F|s2cid=104387714|display-authors=etal}} and Salacia prinoides.{{cite journal|last=Tanabe|first=G|year=2008|title=Synthesis and Elucidation of Absolute Stereochemistry of Salaprinol, another Thiosugar Sulfonium Sulfate from the Ayurvedic Traditional Medicine Salacia prinoides|journal=Tetrahedron|volume=64|issue=43|pages=10080–10086|doi=10.1016/j.tet.2008.08.010|display-authors=etal}} Albomycins are a group of tetrahydrothiophene-ring containing antibiotics from streptomyces while biotin and neothiobinupharidine (and other nuphar alkaloids

{{cite journal|last=Korotkov|first=A|year=2015|title=Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids|journal=Angewandte Chemie International Edition|volume=54|issue=36|pages=10604–10607|doi=10.1002/anie.201503934|pmid=26205039|display-authors=etal|pmc=4691328}}), are examples of bicyclic and polycyclic tetrahydrothiophene-ring containing natural products, respectively.

Because of its smell, tetrahydrothiophene has been used as an odorant in LPG, albeit no longer in North America. It is also used as an odorant for natural gas, usually in mixtures containing tert-butylthiol.

Tetrahydrothiophene is a Lewis base classified as a soft base and its donor properties are discussed in the ECW model.

• Tetrahydrofuran
• Thiophene

{{reflist}}

Category:Thiolanes

Category:Solvents

Category:Foul-smelling chemicals