Benzene derivatives are typically very poor diene partners in classical Diels–Alder (DA) reactions, because of the requirement to dearomatize the benzene ring. Arynes are one of the few classes of dienophiles sufficiently reactive to capture benzene derivatives. We have used a benzyne generated by the hexadehydro-Diels-Alder (HDDA) reaction (cf. 2 from 1) to explore the relative reactivity of various aromatic dienes. The results of intramolecular competitions between pairs of potential trapping agents will be presented (cf. 2 to 3). Some of the resulting DA adducts from this study, upon exposure to visible light, undergo further rearrangement to unusual polycyclic products.

Intramolecular Diels–Alder reactions between aromatic dienes and a benzyne dienophile: Relative reactivities of the dienes

249th National Meeting (2015)

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