The metal-ammonia reduction of 1-acetylnaphthalenes

1-Acetyl-3,4-dihydronaphthalene appears to be the usual reduction product of the reaction without mention of any detection of the expected 1,4-dihydro product. However, sodium-ammonia reductions of 1-acetylnaphthalene and its 4-methyl and 4-ethyl derivatives provide the corresponding 1,4-dihydro pro...

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Veröffentlicht in:	J. Org. Chem.; (United States) 1983-11, Vol.48 (22), p.4149-4150
Hauptverfasser:	Rabideau, Peter W, Husted, Cynthia A, Young, D. Michael
Format:	Artikel
Sprache:	eng
Schlagworte:	400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987) ADDITIVES Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids ALKALI METALS ALKANES ALKENES AMMONIA AMMONIUM CHLORIDES AMMONIUM COMPOUNDS AMMONIUM HALIDES AQUEOUS SOLUTIONS AROMATICS CHEMICAL REACTION YIELD CHEMICAL REACTIONS Chemistry CHLORIDES CHLORINE COMPOUNDS CONDENSED AROMATICS CYCLOALKENES DATA DISPERSIONS ELEMENTS Exact sciences and technology EXPERIMENTAL DATA FURANS HALIDES HALOGEN COMPOUNDS HETEROCYCLIC COMPOUNDS HYDRIDES HYDROCARBONS HYDROGEN COMPOUNDS INFORMATION INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY KETONES LOW TEMPERATURE METALS MIXTURES NITROGEN COMPOUNDS NITROGEN HYDRIDES NMR SPECTRA NUMERICAL DATA Organic chemistry ORGANIC COMPOUNDS ORGANIC OXYGEN COMPOUNDS OXYGEN COMPOUNDS Preparations and properties REDUCTION SODIUM SOLUTIONS SPECTRA TEMPERATURE DEPENDENCE TETRAHYDROFURAN WATER YIELDS
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Zusammenfassung:	1-Acetyl-3,4-dihydronaphthalene appears to be the usual reduction product of the reaction without mention of any detection of the expected 1,4-dihydro product. However, sodium-ammonia reductions of 1-acetylnaphthalene and its 4-methyl and 4-ethyl derivatives provide the corresponding 1,4-dihydro products in essentially quantitative yields. These products appear to be stable and no facile conversion to the conjugated isomers was noted.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo00170a067