The Nef Reaction on 9,10-Dihydro-(11-nitroethano)-anthracenes. A New Route to 9,10-Dihydro-(11-ketoethano)-anthracenes

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

Research output: Contribution to journalArticle

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Abstract

The application of the Nef reaction to the salts of the three most readily available secondary nitro 9,10-dihydro-9,10- ethanoanthracenes is reported. Two of the ketones corresponded in physical properties to samples previously prepared by other methods; the third was previously unknown. It was converted by Clemmensen reduction to a hydrocarbon, 9,10- dihydro-9,10-(11-phenylethano)-anthracene, which was synthesized independently by the Diels-Alder reaction of anthracene with styrene, thus establishing that no rearrangement had taken place during the formation of the ketone.

Original languageEnglish (US)
Pages (from-to)2233-2236
Number of pages4
JournalJournal of the American Chemical Society
Volume78
Issue number10
DOIs
StatePublished - May 1 1956

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