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Ring-Opening Reactions of Aminocyclopropanes

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Synthesis and Reactivity of Donor-Acceptor Substituted Aminocyclopropanes and Aminocyclobutanes

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

Abstract

When I began the project, the intermolecular annulations using DA aminocyclopropanes were unknown.

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Notes

  1. 1.

    http://www.chem.wisc.edu/areas/reich/pkatable/index.htm.

  2. 2.

    Overall yield of the reaction is 96 % with 24 % yield of open product.

  3. 3.

    204 and 205 were also tested unsuccessfully.

  4. 4.

    The diastereospecificity of the reaction will be discussed in the mechanism part of this chapter.

  5. 5.

    The same phenomenon was observed in the project with ketones.

  6. 6.

    Iron trichloride gave comparable results, but the alumina-supported reagent was preferred because it is easier to handle and known to be a scavenger of adventitious traces of water and acid. For examples on the use of FeCl3–Al2O3, see [9, 10].

  7. 7.

    See supporting information.

  8. 8.

    See experimental part for more details.

  9. 9.

    See supporting information for more details.

  10. 10.

    See experimental part for the full table of results

  11. 11.

    See experimental part for full tables of optimization. Concentration and stoichiometry were tested without significant improvements.

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Authors and Affiliations

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

    Florian de Nanteuil

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  1. Florian de Nanteuil
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Correspondence to Florian de Nanteuil .

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de Nanteuil, F. (2016). Ring-Opening Reactions of Aminocyclopropanes. 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_2

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