Reactive intermediates in Diels-Alder cycloadditions

CHED 433

Kitior Fofung, kf150946@reddies.hsu.edu and Jay P Deville, devillej@hsu.edu. Department of Chemistry, Henderson State University, 1100 Henderson Street, Arkadelphia, AR 71999-0001
Diels-Alder reactions of reactive intermediates were studied. Benzyne dienophiles were generated from aromatic bromides and reacted with furan dienes to produce, after treatment with acid, substituted naphthols. The electronic effect of various substituents on the substitution pattern of the final naphthol was examined. Additionally, the effect of the base chosen to generate the benzyne intermediate on the product regiochemistry was probed. Another reactive intermediate in the Diels-Alder reaction, ortho-quinone dimethides, were also studied as a potential route to substituted naphthalenes.