Sulfolene

Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The occasionally reported pungent smell probably originates from adhering sulfur dioxide. The compound is used as a source of butadiene, but it is a versatile synthetic intermediate. In the laboratory it is used as a solid source of butadiene, into which it decomposes by a reverse cycloaddition. Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The occasionally reported pungent smell probably originates from adhering sulfur dioxide. The compound is used as a source of butadiene, but it is a versatile synthetic intermediate. In the laboratory it is used as a solid source of butadiene, into which it decomposes by a reverse cycloaddition. Sulfolene is formed via a reversible cheletropic reaction between 1,3-butadiene and sulfur dioxide. These compounds are first mixed in an autoclave at about −20 °C with an excess of liquid sulfur dioxide in the presence of small amounts of a phenolic polymerization inhibitor (e.g. hydroquinone or pyrogallol) and either allowed to stand at room temperature for eight days or heated to about 130 °C for 30 minutes.