1968
DOI: 10.1016/s0040-4039(00)76333-7
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A ring-opening reaction of and some cyclisations to the adamantane system. A quasi-favorsky reaction of a β-bromoketone

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Cited by 20 publications
(4 citation statements)
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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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%
“…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.…”
mentioning
confidence: 99%