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Ring Expansions of Nonactivated Aziridines and Azetidines

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Book cover Synthesis of 4- to 7-membered Heterocycles by Ring Expansion

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 41))

Abstract

Ring expansions promoted by ring strain in aziridines and azetidines are reviewed in this chapter, putting emphasis on recent applications from the last decade. This vast subject cannot be surveyed here exhaustively, and the reader will be guided to relevant precedent reviews or key reports. Rather, special attention will be put on selected examples and their mechanistic details, aiming to demonstrate that high selectivity can be reached in these reactions. In this issue, this fast-growing topic has been divided into two distinct chapters, this one dealing with “nonactivated” aziridines and azetidines. Therefore, the reader will only find here examples involving NH- or N-alkylaziridines and N-azetidines as substrates for ring expansions, while N-acyl, N-carbamoyl, or N-tosyl compounds, defined as “activated” substrates, will be presented in the next chapter. This distinction can appear quite arbitrary at first sight but is amply justified by the great difference in reactivity of these distinct substrates. The first part focuses on the ring expansions of nonactivated aziridines into up to seven-membered rings and is further divided into expansions involving the incorporation of one (or more) heteroatoms, followed by ring expansions involving only incorporation of carbon atoms. The same model is then followed for azetidines.

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Authors and Affiliations

  1. Institut Lavoisier de Versailles UMR CNRS 8086, Université de Versailles, 45, avenue des Etats-Unis, 78035, Versailles Cedex, France

    François Couty & Olivier R. P. David

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  1. François Couty
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  2. Olivier R. P. David
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Correspondence to François Couty .

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  1. Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering Ghent University, Ghent, Belgium

    Matthias D’hooghe

  2. Department of Chemistry, Hankuk University of Foreign Studies, Yongin-si, Korea (Republic of)

    Hyun-Joon Ha

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Couty, F., David, O.R.P. (2015). Ring Expansions of Nonactivated Aziridines and Azetidines. In: D’hooghe, M., Ha, HJ. (eds) Synthesis of 4- to 7-membered Heterocycles by Ring Expansion. Topics in Heterocyclic Chemistry, vol 41. Springer, Cham. https://doi.org/10.1007/7081_2015_146

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