Synthese und Reaktionen 1‐substituierter Bicyclo‐[2,2,2]‐octane. Untersuchungen in der Bicyclo‐[2,2,2]‐octan‐Reihe, 2. Mitteilung

Grob, C. A.; Ohta, Masaki; Renk, E.; Weiß, Andreas

doi:10.1002/hlca.19580410504

Cited by 70 publications

(26 citation statements)

References 16 publications

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“…After removal of the solvents under reduced pressure crude 5 (1.0 g, 89%) remained in form of a white solid, which was sublimed twice and then completely purified by preparative VPC (20% carbowax 20M on chromosorb R NAW, 60/80 mesh, 4m; oven temp. : 120°C 6 by means of a modified Cristol-Firth-Hunsdiecker reactionz9): The acid (1.2 g, 7.8 mmol) and red mercuric oxide (2.0 g, 9.2 mmol) in 30 ml of dibromomethane were heated to 75°C; bromine (1.3 g, 8.1 mmol) in 5 ml of dibromomethane was added, and the mixture was stirred for 9 h at that temperature. After cooling and filtration the solution was washed with aqueous NaHSO, and brine.…”

Section: (S)mentioning

confidence: 99%

Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo[2.2.2]octane, and of Related 1,4‐Dihalobicyclo[2.2.2]octanes

et al. 1987

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The assignment of the PE spectra of 1-substituted and of 1,Cdisubstituted bicyclo[2.2.2]octanes or related cage-molecules can present serious difficulties, which have to be kept in mind when attempting a rationalization of such an assignment in terms of qualitative concepts. As long as the molecules consist only of first and second row atoms, the usual ab initio or semiempirical models provide a rather safe basis as we shall see by discussing in detail the PE spectra of l-ethynylbicyclo[2.2.2]octane (1) and of 1,4-diethynylbicyclo[2.2.2]octane (2). However, the problem becomes more involved when the substituents are heavy atoms, e.g., halogen atoms. Thus a recent investigation of the He(Ia) PE spectra of symmetrical 1 ,4-dihalonorbonanes2) has shown that the assignment of such spectra is anything but straightforward. Extensive mixing between the substituent and parent-molecule orbitals does no longer allow a unique classification of the observed PE bands as e.g. dominantly n; ' or D-' bands.Schrtne I

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Section: (S)mentioning

confidence: 99%

Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo[2.2.2]octane, and of Related 1,4‐Dihalobicyclo[2.2.2]octanes

et al. 1987

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“…As noted earlier, 6-substituted products such as 3a or 3b may arise by the directing influence of the nitrogen substituent on furan 2a or 2c. Molecular modeling considerations lead to a good prediction of the (8) Freidman, L.; Lugullo, F. M, J. Org, Chem. 1969, 34, 3089 observed regiochemistry in most cases.…”

Section: Scheme P R=ch2ch2n(ch2ch2)2nc6h5-o-och3mentioning

confidence: 99%

Investigations into a mild Diels-Alder approach to 6-substituted quinazoline-2,4-dione derivatives

McNally¹,

Press²

1991

J. Org. Chem.

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1.42 mL) was stirred at 0 °C for 1.5 h. After addition of brine (2 mL), the mixture was extracted with ethyl acetate (3X3 mL).The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by chromatography to yield 23 (57 mg, 65%) as an oil:-2.29°(c 1.245, CHC13); IR (neat) 3460, 1720, 1710,1660 cm'1; NMR (CdCl3) S 1.46 (s, 9 H), 2.38-2.42 (m, 2 H), 2.99 (br s, 1 H), 3.72 (s, 3 H), 3.58-3.76 (m, 2 H), 3.82-4.07 (m, 2 H), 5.41 (d, J = 9.0 Hz, 1 H), 5.92 (d,

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“…After removal of the solvents under reduced pressure crude 5 (1.0 g, 89%) remained in form of a white solid, which was sublimed twice and then completely purified by preparative VPC (20% carbowax 20M on chromosorb R NAW, 60/80 mesh, 4m; oven temp. : (6): Bicyclo[2.2.2]octane-l -carboxylic acid was converted into the bromo derivative 6 by means of a modified Cristol-Firth-Hunsdiecker reactionz9): The acid (1.2 g, 7.8 mmol) and red mercuric oxide (2.0 g, 9.2 mmol) in 30 ml of dibromomethane were heated to 75°C; bromine (1.3 g, 8.1 mmol) in 5 ml of dibromomethane was added, and the mixture was stirred for 9 h at that temperature. After cooling and filtration the solution was washed with aqueous NaHSO, and brine.…”

Section: Synthesis Of the L-halobicyclo[222]octanes Bicyclo[222 ]mentioning

confidence: 99%

ChemInform Abstract: Small and Medium Rings. Part 62. Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo(2.2.2)octane, and of Related 1,4‐Dihalobicyclo(2.2.2)octanes.

Honegger¹,

Heilbronner²,

Hess³

et al. 1987

ChemInform

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Synthese und Reaktionen 1‐substituierter Bicyclo‐[2,2,2]‐octane. Untersuchungen in der Bicyclo‐[2,2,2]‐octan‐Reihe, 2. Mitteilung

Cited by 70 publications

References 16 publications

Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo[2.2.2]octane, and of Related 1,4‐Dihalobicyclo[2.2.2]octanes

Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo[2.2.2]octane, and of Related 1,4‐Dihalobicyclo[2.2.2]octanes

Investigations into a mild Diels-Alder approach to 6-substituted quinazoline-2,4-dione derivatives

ChemInform Abstract: Small and Medium Rings. Part 62. Synthesis and PE Spectra of 1‐Ethynyl‐ and 1,4‐Diethynylbicyclo(2.2.2)octane, and of Related 1,4‐Dihalobicyclo(2.2.2)octanes.

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