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Synthesis and stereochemistry of 8-methyl-5-nitro-1-octalones

Synthese und Stereochemie von 8-Methyl-5-nitro-octalonen

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Base catalyzedMichael addition of 5-nitropentan-2-one ethylene ketal (1) and cyclohex-2-enone (2), subsequent deprotection, and intramolecular aldol condensation yields the 8-methyl-5-nitro-1-octalone isomers (5a,b). The structure, relative configuration, and conformation of5a and5b were elucidated utilizing the results of1H and13C NMR investigations

Zusammenfassung

BasenkatalysierteMichael-Addition von 5-Nitropentan-2-on-ethylenketal (1) und Cyclohex-2-enon (2), anschließende Entfernung der Schutzgruppe und darauffolgende Aldolkondensation liefert isomer 8-Methyl-5-nitro-1-octalone (5a,b). Struktur, relative Konfiguration und Konformation von5a und5b wurden mittels1H- und13C-NMR-Spektroskopie aufgeklärt.

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References

  1. Cook CE, Whichard LP, Wall ME, Egley GH, Coggon P, Luhan PA, McPhail AT (1972) J Am Chem Soc94: 6198

    Google Scholar 

  2. Pepperman AB, Connick WJ, Vail SL, Worsham AD, Pavlista AD, Moreland DE (1982) Weed Sci 561

  3. Kádas I, Árvai G, Töke L, Tóth G, Szöllösy Á, Bihari M (1994) Tetrahedron50: 2895

    Google Scholar 

  4. Tóth G, Halász J, Kádas I, Árvai G, Mikló K, Haeßner R (1995) Magn Reson Chem33: 184

    Google Scholar 

  5. Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) J Am Chem Soc107: 3902

    Google Scholar 

  6. Haasnoot CAG, de Leeuw FAAM, Altona C (1980) Tetrahedron36: 2783

    Google Scholar 

  7. Subramanian S, Bax A (1987) J Magn Reson71: 325

    Google Scholar 

  8. Kinns M, Sanders JKM (1984) J Magn Reson56: 518

    Google Scholar 

  9. Bax A, Subramanian S (1986) J Magn Reson67: 565

    Google Scholar 

  10. ApSimon JW, Craid WG, Demarco PV, Mathieson DV, Saunders L, Whalley WB (1967) Tetrahedron23: 1967

    Google Scholar 

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Authors and Affiliations

  1. Technical Analytical Research Group of the Hungarian Academy of Science, Institute for General and Analytical Chemistry, Technical University of Budapest, H-1111, Budapest, Hungary

    J. Halász & G. Tóth

  2. Research Group of the Hungarian Academy of Science, Department of Organic Chemical Technology, Technical University of Budapest, H-1521, Budapest, Hungary

    I. Kádas, G. Árvai & K. Mikló

  3. Technische Universität München, Organisch-Chemisches Institut, D-85747, Garching, Germany

    R. Haeßner

Authors
  1. J. Halász
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  2. G. Tóth
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  3. I. Kádas
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  4. G. Árvai
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  5. K. Mikló
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  6. R. Haeßner
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Halász, J., Tóth, G., Kádas, I. et al. Synthesis and stereochemistry of 8-methyl-5-nitro-1-octalones. Monatsh Chem 126, 1011–1019 (1995). https://doi.org/10.1007/BF00811021

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  • DOI: https://doi.org/10.1007/BF00811021

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