Rearrangement of 1-NN-dichloroaminoadamantane catalysed by aluminium chloride

Kovacic, Peter; Liu, Jih-Hua; Roskos, Philip D.; Levi, E.

doi:10.1039/c29700001034

Cited by 4 publications

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“…The desired product was separated from the dark brown residue by preparative glpc. Sublimation provided 7 which was identical in all respects with the corresponding product obtained from catalytic hydrogenation of 1 at 130°.…”

Section: Methodsmentioning

confidence: 66%

“…The solution was stirred at room temperature for 15 min and then at 60-70°for 45 min. After the cooled mixture was poured into 100 ml of water, the filtered solid was recrystallized from benzene, affording 0.74 g (70%) of the dibenzamide: mp 208-209°; ir (KBr) 3300 (NH), 1650 (C=0), and 1550 cm-1 (NH); nmr (CDCI3) 3.26 (t, 2, CH2N), 4.43 (broad s, 1, CHN), 6.10 (broad d, 1, NH), 6.63 (broad m, 1, NH), 7.41 (m, 5, Ar), 7.80 (m, 5, Ar).…”

Section: Methodsmentioning

confidence: 99%

“…Reductions wherein lithium aluminum hydride has been used have given conflicting results. [7][8] We have found that a three-step procedure involving two reduction-dehydration sequences using sodium borohydride in methanol or 2-propanol converts many anthraquinones (1) to anthracenes (5) in a straightforward fashion, via the successive formation of 9,10-dihydroxy-9.10-dihydro intermediates, enthrones, and 9-hydroxy-9.10-dihydro intermediates. The steps are schematically represented wherein X represents one or more substituents on either or both end rings.…”

Section: Methodsmentioning

confidence: 99%

“…In previous, related studies involving 1, Wolff-Kishner reduction6 provided endo-3-bicyclo-[3.3.Ijnonylmethylamine, and LÍAIH4 gave 4-azahomoadamantane. 7 Results and Discussion Hydride Reduction. Initially, our attention was focused on reduction of 1 with sodium borohydride in various alcoholic solvents.…”

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confidence: 99%

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Adamantanes and related compounds. VIII. Behavior of endo-7-aminomethylbicyclo[3.3.1]nonan-3-one under reducing conditions

Tonnis¹,

Wnuk²,

Dolan³

et al. 1974

J. Org. Chem.

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The behavior of toward various reducing agents was investigated. Sodium borohydride gave a mixture of endo and exo alcohols (mainly endo) whose ratio varied depending upon the nature of the alcohol used as the medium. Sodium-alcohol reduction provided the exo alcohol as essentially the only product. With hydrogenation in ethanol in the presence of Raney nickel, carbonyl reduction, N-alkylation, and reductive cyclization occurred. Either mono-or dialkylation on nitrogen took place depending upon the temperature. The cyclization reaction produced A-ethyl-4-azahomoadamantane. Conversion to the diamine, exo-3-amino-endo-7-aminomethylbicyclo[3.3.1]nonane, was effected by sodium-ethanol reduction of the oxime of 1. Mechanistic and conformational aspects are also treated.There are relatively few uncomplicated routes for entry into the bicyclo[3.3.1]nonane series.4"6 A simple pathway was recently reported6'7 via rearrangement of l-N,N-dichloroaminoadamantane in the presence of aluminum chloride. Subsequent exposure to aqueous acid afforded endo-7-aminomethylbicyclo[3.3.1]nonan-3-one (1) in 70-80% yield (eq 1). Prior work6•8 has shown that 1 can serve as a versatile precursor for a variety of derivatives in this series by reactions which generally take place in high yield.

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Section: Methodsmentioning

confidence: 66%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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