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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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Article information


Submitted
19 Dec 2016
Accepted
21 Mar 2017
First published
24 Mar 2017

This article is Open Access

RSC Adv., 2017,7, 18211-18216
Article type
Paper

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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