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Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

Part of the book series: Springer Theses ((Springer Theses))

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Abstract

All reactions were carried out in oven-dried glassware under nitrogen or argon atmosphere with magnetic stirring, unless stated otherwise. THF, Et2O, CH3CN, toluene, hexane and dichloromethane were dried by passage over activated alumina under nitrogen atmosphere (water content <30 ppm, Karl-Fischer titration) on an Innovative Technology Solvent Delivery System.

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Notes

  1. 1.

    The diazo carbon could not be detected.

  2. 2.

    One carbon aliphatic of one diastereoisomer could not be resolved.

  3. 3.

    The CH3 carbons of TIPS are splitting.

  4. 4.

    Not all the signals of the minor diastereoisomer were resolved by 13C.

  5. 5.

    Peaks are splitting due to conformers of methyl ester.

  6. 6.

    The diazo carbon could not be detected.

  7. 7.

    One of the aromatic carbons is overlapping.

  8. 8.

    Some phthalimide peaks could not be resolved.

  9. 9.

    Measured at 268 K.

  10. 10.

    An impurity is present in approx. 5 % in 1H NMR spectrum.

  11. 11.

    Measured at 268 K.

  12. 12.

    Measured at 268 K. The carbon atoms of the phthalimide group are not equivalent.

  13. 13.

    The phthalimide peaks of the trans diastereomer could not be resolved due to NMR exchange.

  14. 14.

    Only one CF3 peak could be detected.

  15. 15.

    Two carbonyls peaks are not overlapping.

  16. 16.

    All carbons couldn’t be resolved.

  17. 17.

    The integration differs from the reported values but the overall number of protons is correct.

  18. 18.

    Argon from gas cylinder was used as using central nitrogen supply with Drierite filter gave blue complexes.

  19. 19.

    Blue complex gave lower er and poorly reproducible results.

  20. 20.

    Dried by dissolving in benzene then removing the solvent under reduced pressure and drying in high vacuo.

  21. 21.

    2 carbon signal overlapping.

  22. 22.

    Structure is registered in CCDC under the number CCDC 988525.

  23. 23.

    Due to shoulder in the peaks, separation was not complete (cf HPLC spectra).

  24. 24.

    The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 933180.

  25. 25.

    The methylenation crude was used directly without isolation of methylenemalonate compound.

  26. 26.

    Two peaks under this signal as determined by HMBC.

  27. 27.

    A peak is not resolved in the 128.45–128.40 massif.

  28. 28.

    The deuterated carbon was not resolved.

  29. 29.

    One peak corresponding to the Me of TBDMS has been cut due to small acquisition window.

  30. 30.

    HRMS could not be detected for this compound.

  31. 31.

    Carbon with fluoride not resolved.

  32. 32.

    Two peaks of the TBS have been cut during analysis. One aromatic peak overlapped.

  33. 33.

    2 peaks overlap.

  34. 34.

    Peaks of impurities are present in the aromatic area.

  35. 35.

    NH2 peak over-integrated due to water in CDCl3.

  36. 36.

    No yield was recorded.

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  1. Institut des Sciences et Ingénierie Chimiques, Swiss Federal Institute of Technology in Lausanne, Lausanne, Switzerland

    Florian de Nanteuil

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de Nanteuil, F. (2016). Experimental Part. In: Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-23006-1_5

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