Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes
Abstract
:Introduction
Results and Discussion
Educt | Product | Yield [%] from 1 | Yield [%] from PCA | Ref. |
Furan | 2a | 54 | 57 | [1,3] |
Cyclopentadiene | 2b | 39 | 57 | [4] |
Spiro[2.4]hepta-4,6-diene | 2c | 45 | 49 | [a] |
2-Methylfuran | 2d | 44 | 66 | [4] |
2,5-Dimethylfuran | 2e | 47 | 68 | [4] |
2-(But-3-enyl)-3-methylfuran | 2f | 51 | 88 | [4] |
3-Methyl-2-(3-methylbut-3-enyl)furan | 2g | 45 | 87 | [4] |
Conclusions
Experimental
General
2,2-Dichloro-1-(trichloromethyl)ethenyl diethyl phosphate (1)
Reaction of 1 with Sodium 2,2,2-trifluoroethoxide in 2,2,2-Trifluoroethanol — Diethyl (2,2,2-trifluoro-ethyl) phosphate (3), 2,2,2-Trifluoroethyl 2,3,3-trichloroprop-2-enoate (6) and 2,2,2-Trifluoroethyl dichloroacetate (9)
2,2,4,4-Tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-one (2a).
2,2,4,4-Tetrachlorobicyclo[3.2.1]oct-6-en-3-one (2b).
2,2,4,4-Tetrachloro-spiro(bicyclo[3.2.1]oct-6-ene-8,1'-cyclopropane)-3-one (2c)
1-Methyl-2,2,4,4-tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-one (2d)
1,5-Dimethyl-2,2,4,4-tetrachloro-8-oxabicyclo[3.2.1]oct-6-en-3-one (2e)
1-(But-3-enyl)-2,2,4,4-tetrachloro-7-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (2f)
2,2,4,4-Tetrachloro-7-methyl-1-(3-methylbut-3-enyl)-8-oxabicyclo[3.2.1]oct-6-en-3-one (2g)
Acknowledgements
References and Notes
- Föhlisch, B.; Gehrlach, E.; Herter, R. Angew. Chem. 1982, 94, 144, Angew. Chem. Suppl. 1982, 241–248; Angew. Chem. Internat. Edit. Engl. 1982, 21, 137.
- Herter, R.; Föhlisch, B. Synthesis 1982, 976–978.
- Föhlisch, B.; Gehrlach, E.; Geywitz, B. Chem. Ber. 1987, 120, 1815–1824.
- Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Föhlisch, B. J. Org. Chem. 1999, 64, 3398–3408.
- Föhlisch, B.; Korfant, H.; Meining, H.; Frey, W. Eur. J. Org. Chem. 2000, 1335–1344.
- Föhlisch, B.; Zinser, H. Org. Prep. Procedures Int. submitted.
- Edwards, E. G.; Evans, D. P.; Watson, H. B. J. Chem. Soc. 1937, 1942–1946.Gerrard, W.; Howe, B. K. J. Chem. Soc. 1995, 505–510.Geiger, M.; Usteri, E.; Gränacher, C. Helv. Chim. Acta 1951, 34, 1335–1344.Bugrova, L. V.; Rudnev, G. K.; Khristich, A. I.; Radchenko, V. I.; Mishchenko, L. F. Zh. Prikl. Khim. (Leningrad). 1973, 46, 1529–1533, J. Appl. Chem. USSR 1973, 2, 1627–1631 (Engl. Transl) [Chem. Abstr. 1973, 79, 91499q].
- For some uses, see: Kadaba, P. K.; Edwards, J. O. J. Org. Chem. 1960, 25, 1432–1433.Grant, F. W.; Cassie, W. B. J. Org. Chem. 1960, 25, 1433–1434.Holy, A.; Smrt, J.; Šorm, E. Coll. Czech. Chem. Commun. 1965, 30, 3309–3319.Rudavskii, V. P.; Khaskin, I. G. Ukr. Khim Zh. 1967, 33, 391–394, [Chem. Abstr. 1967, 67, 63963v].Panetta, C. A.; Casanova, T. G. J. Org. Chem. 1970, 35, 2423–2425.Migaichuk, V.; Khaskin, I. G. Zh. Prikl. Khim. (Leningrad). 1970, 50, 2599–2602, J. Appl. Chem. USSR 1977, 50, 2471–2473 (Engl. Transl).Laskovics, F. M.; Schulman, E. M. J. Am. Chem. Soc. 1977, 99, 6672–6677.Magid, R. M.; Talley, B. G.; Souther, S. K. J. Org. Chem. 1981, 46, 824–825.Freedlander, R. S.; Bryson, T. A.; Dunlap, R. B.; Schulman, E. M.; Lewis, C. A. J. Org. Chem. 1981, 46, 3519–3521.Talley, J. J. Tetrahedron Lett. 1981, 22, 823–826.Bew, C.; Otero de Joshi, V.; Gray, J.; Kaye, P. T.; Meakins, G. D. J. Chem. Soc. Perkin Trans. 1 1982, 945–848.Hrubiec, R. T.; Smith, M. B. Synth. Commun. 1983, 13, 593–599.Hrubiec, R. T.; Smith, M. B. J. Org. Chem. 1984, 49, 431–435.
- Wiley, D. W.; Simmons, H. E. J. Org. Chem. 1964, 29, 1876–1879.
- Nikonorov, K. V.; Neklesova, I. D.; Gutylev, E. A.; Kudrina, M. A.; Nikonenko, V. A.; Mertsalova, F. F.; Anisimova, N. N.; Iraidova, I. S.; Egorova, N. V.; Lisanova, I. A. Zh. Obshch. Khim. 1974, 44, 1267–1272, J. General Chem. USSR 1974, 44, 1245–1250 (Engl. Transl.).
- Perkow, W. Chem. Ber. 1954, 87, 755–758.b) For an overview, see, e.g. Krauch, H.; Kunz, W. Reaktionen der organischen Chemie, 6th edition; (Kunz, W.; Nonnenmacher, E., Eds.); Hüthig Verlag: Heidelberg, 1997; pp. 634–636. [Google Scholar] and the literature cited therein
- Timperley, C. M.; Morton, I. J.; Waters, M. J.; Yarwood, J. L. J. Fluorine Chem. 1999, 96, 95–100.
- Filonenko, L. P.; Bespal'ko, G. K.; Marchenko, A. P.; Pinchuk, A. M. Zh. Obshch. Khim. 1987, 57, 2320–2324, J. Gen. Chem. USSR 1987, 57, 2074–2078 [Chem. Abstr. 1988, 109, 129086f] — However, the required reagents would be more expensive.
- Hesse, G. Methoden der Organischen Chemie (Houben-Weyl); Bayer, O., Kropf, H., Hesse, G., Eds.; Thieme: Stuttgart, 1978; Vol. 6/1d, pp. 130–133, and the literature cited therein. [Google Scholar]
- Levina, R. Ya.; Mezentsova, N. N.; Lebedev, O. V. Zh. Obshch. Khim. 1955, 29, 1097–1101, J. Gen. Chem. USSR. 1955, 25, 1055–1057 (Engl. Transl.).Hallam, B. F.; Pauson, P. L. J. Chem. Soc. 1958, 646–650.Alder, K.; Ache, H. J.; Flock, F. H. Chem. Ber. 1960, 93, 1888–1895.Kunitake, T.; Ochiai, T. Macromol. Synth. 1985, 9, 61–63.
- Prepared by Uwe Wustmann in the course of the Organisch-chemisches Praktikum für Fortgeschrittene, February, 8 – May, 8, 1988.
- The 1H-NMR spectrum appears to be deceptively simple, as indicated by a Gauß pulsed recording.
- Scott, L. T.; Naples, J. D. Synthesis 1973, 209.
- Kaiser, R.; Föhlisch, B. Helv. Chim. Acta 1990, 73, 1504–1514.
- Firmenich SA (Schulte-Elte, K. H.). Swiss Patent 603614; (6.10.1975) [Chem. Abstr. 1979, 90, P6234j],Kaiser, R. Dissertation, Univ. Stuttgart, 1986.
- Sample Availability: Samples of compounds 2a, 2b, 2c, 2d, 2e, 2f and 2g are available from MDPI
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Föhlisch, B.; Reiner, S. Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes. Molecules 2004, 9, 1-10. https://doi.org/10.3390/90100001
Föhlisch B, Reiner S. Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes. Molecules. 2004; 9(1):1-10. https://doi.org/10.3390/90100001
Chicago/Turabian StyleFöhlisch, Baldur, and Stefan Reiner. 2004. "Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes" Molecules 9, no. 1: 1-10. https://doi.org/10.3390/90100001