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Maleic Anhydride pp 103–146Cite as

Diels-Alder Reaction

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Abstract

In this chapter, we will consider the one reaction of maleic anhydride that has been most investigated in the last half-century. Of historical significance is the formation of a cyclohexene derivative 3 from a conjugated diene (butadiene) 2 and a dienophile (maleic anhydride, MA) 1 as reported by Otto Diels and Kurt Alder in 1928.(1)* This reaction is called the Diels-Alder (DA) reaction, diene synthesis, or the [4 + 2] cycloaddition reaction. The role that MA has played in this reaction along with other dienophiles cannot possibly be covered in a single chapter such as this. The impetus it provided to synthetic organic research, particularly in the fields of steroids, polycyclic aromatics, and alkaloids, by allowing a one-step ring closure, can barely be exemplified in a treatment such as this. The efforts of Diels and Alder were duly recognized by a Nobel Prize for chemistry in 1950.(2)

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    B. C. Trivedi & B. M. Culbertson

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Trivedi, B.C., Culbertson, B.M. (1982). Diels-Alder Reaction. In: Maleic Anhydride. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-0940-7_4

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