Chemistry help needed on the practical advantage of the use of 3-sulfolene as the source of 1,3-butadiene

Anonymous
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what practical advantage does the use of 3-sulfolene as the source of 1,3-butadiene provide over directly using 1,3-butadiene during a diels-alder experiment?

Tutor Answer

IRINI
School: New York University

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When 1,3-butadiene and dienophiles react with a Diels-Alder mechanism, the reactivity is low and usually requires prolonged heating above 100 °C. Consequently, if neat butadiene is used, special equipment for work under elevated pressure is also required making the whole procedure rather dangerous. Sulfolene can be used as an alternative to generate butadiene in situ by thermal sulfur dioxide extrusion.  In this case we don’t expect buildup of butadiene pressure as the released diene is consumed in the cycloaddition, and therefore the equilibrium of the reversible extrusion reaction acts as an internal “safety valve”. This is the practical advantage of the use of 3-sulfolene as the source of 1,3-butadiene provide over directly using 1,3-butadiene during a diels-alder experiment


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Anonymous
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