A ring-opening reaction of and some cyclisations to the adamantane system. A quasi-favorsky reaction of a β-bromoketone

Udding, A.C.; Wynberg, Hans; Strating, J.

doi:10.1016/s0040-4039(00)76333-7

Cited by 20 publications

(4 citation statements)

References 13 publications

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“…The ring opening of diamondoids was initially studied in the 1960s, [18,19] but in those cases only for compounds with the adamantane skeleton. For example, Sasaki et al [19] studied the reaction of adamantan-2-one with sodium azide in methanesulfonic acid.…”

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Synthesis and mass spectrometry of some tri‐and tetracyclic naphthenic acids

Rowland

Clough

West

et al. 2011

Rapid Comm Mass Spectrometry

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confidence: 99%

Synthesis and mass spectrometry of some tri‐and tetracyclic naphthenic acids

Rowland

Clough

West

et al. 2011

Rapid Comm Mass Spectrometry

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“…Attack of oxygen by the cation in 23 (see below) would yield 20. Alternatively, 22 may serve directly as precursor to 20 via displacement of molecular nitrogen by the nucleophilic hydroxyl group. Rearrangement of 23 by a 1,2-hydride shift generates the more stable tertiary ion 24.…”

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“…In addition, 30 provided 28 with sulfuric acid. 22 In deamination of a related compound 34, involvement of the electrons with the electrophilic site is not feasible at the initial stage29 (Scheme V). With the isomeric amine, products the alkene function is unfavorably situated stereochemically for assisting in displacement.…”

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Adamantanes and related compounds. XII. Diazotization of endo-7-aminomethylbicyclo[3.3.1]nonan-3-ols and endo-7-aminomethylbicyclo[3.3.1]non-2-ene

Wnuk¹,

Tonnis²,

Dolan³

et al. 1975

J. Org. Chem.

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Diazotization of endo-7-aminomethylbicyclo[3.3.1]nonan-exo-3-ol (3) with aqueous nitrous acid produced 3methylbicyclo[3.3.1]non-2-en-eio-7-ol (7), exo-7-methylbicyclo[3.3.1]nonan-3-one (8), and presumably exo-8-hydroxybicyclo[4.3.1]dec-2-ene (9) as major products. Exposure of endo-7-aminomethylbicyclo[3.3.1]nonan-endo-3-ol (2) to both protic (acetic acid or water) and aprotic (benzene) deamination resulted mainly in formation of 1methyl-2-oxaadamantane (19) and 4-oxahomoadamantane (20) in addition to a component tentatively identified as endo-8-hydroxybicyclo[4.3.1]dec-3-ene (21). Compound 2 yielded endo-7-aminomethylbicyclo[3,3.1]non-2-ene (4) with dilute sulfuric acid. Deamination of 4 under conditions used for 2 provided 2-adamantanol (28) and 2adamantyl acetate (29) as principal products. Elimination, transannular interactions, and apparently ring expansion comprise the dominant reaction routes. 7 gave 8 with sulfuric acid. The preparations of the isomeric 7-methylenebicyclo[3.3.l]nonan-3-ols (10) and endo-7-methylbicyclo[3.3.l]nonan-3-one (11) from reduction of 7-methylenebicyclo[3.3.l]nonan-3-one (12) are described. Endo alcohol 10b provided 19 under acidic conditions. Mechanistic aspects of the investigation are treated.

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“…A single product 5 was formed when the pyridinium salt 1 was allowed to stand for 2 days at room temperature in an excess of the nitrone 2 (Scheme I). Spectroscopic data indicated that 5 was a 1,4-dihydropyridine formed through the condensation between 1 and 2 with the loss of toluenesulfonic acid: mass spectrum m/e 438 (M+); nmr 4.20 ppm (1 H, doublet, J = 3 Hz, proton at C4 in the dihydropyridine nucleus); Xmax (MeOH) 220 nm (e 30,900), 265 (15,100), and 353 (8750)A3 These data, when interpreted within the framework of known nitrone chemistry,4 suggest that the position of attachment to the nitrone ring is at the 3'-carbon atom rather than the 5'-carbon atom, which cannot be excluded on the basis of the spectroscopic data alone. Support for this structure assignment was provided by the condensation between S.S-dimethyl-AKpyrroline 1oxide (3) and 1.…”

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confidence: 99%