The Diels-Alder Reaction of Anthracene with Nitroölefins. A New Route to 11-nitro- and 11-amino-9,10-Dihydro-9,10-Ethanoanthracenes

Wayland E. Noland, Howard I. Freeman, M. Scott Baker

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12 Scopus citations

Abstract

The preparation of a series of seven Diels-Alder adducts of anthracene and common nitroolefins unsubstituted, 1- or 2- monosubstituted or 1,2- or 2,2-disubstituted is described; in the latter two cases the practical limits of the reaction appear to have been reached. The four adducts obtained in the best yields (19-62%) have been converted to the corresponding amines and their derivatives. The ultraviolet spectra of all the compounds compare favorably with the spectra of dihydroanthracenes reported in the literature.

Original languageEnglish (US)
Pages (from-to)188-192
Number of pages5
JournalJournal of the American Chemical Society
Volume78
Issue number1
DOIs
StatePublished - Jan 1 1956

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