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Efficient strategy toward saturated N,P-heterocycles. Synthesis of l,2-azaphospholidines and extension to the preparation of azaphosphacane and azaphosphanane higher homologues

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Abstract

Access to a new family of saturated N,P-heterocycles is described. Allylphosphonochloridates react with primary amines through a single synthetic operation involving the formation of N–P and N–C bonds to afford l,2-azaphospholidines. The N–P bond formation/aza-Michael cyclization sequence is extended to eight- and nine-membered N,N,P-heterocycles. The first lines of a conformational study of diazaphosphacanes are described. DFT calculations allowed the identification of two diastereomers that display preferred boat-chair and twisted-boat-chair conformations.

Graphical abstract: Efficient strategy toward saturated N,P-heterocycles. Synthesis of l,2-azaphospholidines and extension to the preparation of azaphosphacane and azaphosphanane higher homologues

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Publication details

The article was received on 19 Dec 2016, accepted on 21 Mar 2017 and first published on 24 Mar 2017


Article type: Paper
DOI: 10.1039/C6RA28420E
RSC Adv., 2017,7, 18211-18216
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    Efficient strategy toward saturated N,P-heterocycles. Synthesis of l,2-azaphospholidines and extension to the preparation of azaphosphacane and azaphosphanane higher homologues

    H. Boufroura, A. Abdelli, F. Bourdreux, A. Gaucher, G. Clavier, M. L. Efrit, H. M'rabet and D. Prim, RSC Adv., 2017, 7, 18211
    DOI: 10.1039/C6RA28420E

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