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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

Boufroura, H.; Abdelli, A.; Bourdreux, F.; Gaucher, A.; Clavier, G.; Efrit, M. L.; M'rabet, H.; Prim, D., RSC Advances, 2017, 7, 18211-18216.

Références :

RSC Advances, 2017, 7, 18211-18216.

Auteur(s) : 

Boufroura, H.; Abdelli, A.; Bourdreux, F.; Gaucher, A.; Clavier, G.; Efrit, M. L.; M'rabet, H.; Prim, D.

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.


Type :
Publication
Dates :
Paru le 24 mars 2017
Informations complémentaires :
DOI: 10.1039/c6ra28420e

 

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