REDUCTIONS WITH NICKEL-ALUMINUM ALLOY AND AQUEOUS ALKALI. PART VI. NAPHTHALENE AND ITS SUBSTITUTION PRODUCTS¹

Abstract

In a previous publication (1) from these laboratories, the displacement of sulfonic acid groups by the action of a nickel-aluminum alloy in aqueous alkali was reported. In the case of naphthalene sulfonic acids, simultaneous reduction to tetrahydronaphthalenes accompanied hydrogenolysis of the sulfonic acid groups. This paper describes the results of our studies on the application of the Raney alloy reduction procedure to a variety of mono-and di-substituted naphthalene compounds.The hydrogenation of naphthalene and naphthalene derivatives to the corresponding tetrahydro and decahydro compounds has been the subject of many investigations. The classical studies of Bamberger (2) on the reduction of naphthalene derivatives by means of sodium and alcohols established the marked difference in reactivity of the substituted and unsubstituted rings of the naphthols. While -naphthol reduces almost exclusively in the unsubstituted ring to give the phenolic, or-a-tetralol (I), /3-naphthol reduces to the alcohol, ac-ß-

Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: the effect of electron-donating and electron-withdrawing groups

“…The resulting light brown oil was purified by flash chromatography (silica gel 200-400 mesh, 10% AcOEt and 10% CH 2 Cl 2 in hexanes) affording the indan 37 (0.072 g, 0.27 mmol, 37%), 39 (0.028 g, 0.094 mmol, 13%), 38 (0.032 g, 0.12 mmol, 16%), and 40 (0.014 g, 0.065 mmol, 9%). (37 (40). 50 Yellow solid.…”

Nickel-aluminum alloy as a reducing agent

“…Together with findings for a wide variety of other compounds containing the N-N and/or N-0 linkages, these data indicate that hydrogenolysis of such interheteroatom bonds is a fairly general result of treatment with nickel-aluminum alloy (Figure 2) 20>23>29. 50,52,53,69,[110][111][112][113][114][115][116][117][118][119][120] As illustrated in Table X, for instance, C-nitro and -nitroso compounds undergo reduction to the corresponding amines, usually in preparatively significant yield. The course of reduction in basic medium is similar to that in aqueous formic acid, although the Nformyl derivative is usually the major product in the latter solvent.…”

Competitive solvent extraction of alkaline-earth cations into chloroform by lipophilic acyclic diionizable polyethers

“…The sources of reagent grade inorganic chemicals and the methods for solvent purification were the same as before (1). Methyl 5-decylsalicylate (2), methyl 5,6,7,8-tetrahydro-3hydroxy-2-naphthoate (3,4), and diethyl 4-n-decyl-2-hydroxybenzenephosphonate (5) were prepared by known methods. Ethylene, diethylene, triethylene, and tetraethylene glycols were obtained from Aldrich (Milwaukee, WI) and converted into the corresponding ditosylates according to a reported general procedure (6).…”