It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents.
[11] The thermodynamically more stable 2-sulfolene can be isolated from the mixture of isomers as pure substance in the form of white plates (m.p.
[12] Catalytic hydrogenation yields sulfolane, a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon streams.
[7] Thiophene-1,1-dioxide, a highly reactive species, is also accessible via the formation of 3,4-bis(dimethylamino)tetrahydrothiophene-1,1-dioxide and successive double quaternization with methyl iodide and Hofmann elimination with silver hydroxide.
[12] A less cumbersome two-step synthesis is the two-fold dehydrobromination of 3,4-dibromotetrohydrothiophene-1,1-dioxide with either powdered sodium hydroxide in tetrahydrofuran (THF)[14] or with ultrasonically dispersed metallic potassium.
One potential drawback, aside from expense, is that the evolved sulfur dioxide can cause side reactions with acid-sensitive substrates.
With sulfolene no buildup of butadiene pressure could be expected as the liberated diene is consumed in the cycloaddition, and therefore the equilibrium of the reversible extrusion reaction acts as an internal "safety valve".
[17] 6,7-Dibromo-1,4-epoxy-1,4-dihydronaphthalene (6,7-Dibromonaphthalene-1,4-endoxide, accessible after debromination from 1,2,4,5-tetrabromobenzene using an equivalent of n-butyllithium and Diels-Alder reaction in furan in 70% yield[18]) reacts with 3-sulfolene in boiling xylene to give a tricyclic adduct.
[23] With diazomethane, 3-sulfolene forms in a 1,3-dipolar cycloadduct:[24] In 1935, H. Staudinger and co-workers found that the reaction of butadiene and SO2 at room temperature gives a second product in addition to 3-sulfolene.
The reversibility of the interconversion of 3-sulfolene with buta-1,3-diene and sulfur dioxide suggests the use of sulfolene as a recyclable aprotic dipolar solvent, in replacement for dimethyl sulfoxide (DMSO), which is often used but difficult to separate and poorly reusable.
It appears questionable though, if 3-sulfolene with a useful liquid phase range of only 64 to a maximum of about 100 °C can be used as DMSO substitutes (easy handling, low cost, environmental compatibility) in industrial practice.