Abstract
The title compound, C26H38ClN2OP, was synthesized by reacting phosphoryl chloride with N,N'-bis-(2,6-diiso-propyl-phen-yl)ethane-1,2-di-amine in the presence of N-methyl-morpholine which acted as an auxilliary base to quench the HCl released as a by-product. The resultant N-heterocyclic phosphine five-membered ring adopts a half-chair conformation and features a tetra-coordinate P atom ligated by the chelating di-amine [P-N = 1.6348 (14) and 1.6192 (14) Å], one double-bonded O atom [P1-O1 = 1.4652 (12) Å] and one Cl atom [P1-Cl1 = 2.0592 (7) Å]. The sterically hindered 2,6-diiso-propyl-phenyl (Dipp) groups twist away from the central heterocycle, with torsion angles of -75.66 (19) and 83.39 (19)° for the P-N-Car-Car links. A number of intra-molecular C-H⋯N, C-H⋯O and C-H⋯Cl close contacts occur. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds to generate [010] chains. C-H⋯π inter-actions are also observed.
Highlights
The title compound, C26H38ClN2OP, was synthesized by reacting phosphoryl chloride with N,N0 -bis(2,6-diisopropylphenyl)ethane-1,2-diamine in the presence of N-methylmorpholine which acted as an auxilliary base to quench the HCl released as a by-product
The title compound, 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine 2-oxide, is closely related to these compounds and its analogs are commonly used as precursor molecules for the synthesis of pharmaceuticals targeted towards immunosuppressants and chemotherapy medications
Starting material was completely consumed, the reaction mixture was dried in vacuo to give a pale-yellow coloured solid. Extraction of this solid with 50 ml of a 3:2 mixture of pentane:THF produced the desired product as a pale-yellow coloured solution following filtration through Celite, which when dried in vacuo afforded 0.919 g (66%) of the desired product as a faintly yellow coloured powder
Summary
1,3,2-Diazaphospholidines are a class of N-heterocyclic phosphines (NHPs) that feature an N—P—N moiety bridged by a. Derivatives are often substituted by alkyl, aryl, or halogen groups at the phosphorus position (denoted as position 2), allowing them to serve as both ligands and/or precursors in organometallic chemistry (Gudat, 2010). The title compound, 2-chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine 2-oxide, is closely related to these compounds and its analogs are commonly used as precursor molecules for the synthesis of pharmaceuticals targeted towards immunosuppressants and chemotherapy medications The crystal structure of the title compound is reported and features a saturated five-membered NHP substituted at the phosphorus position by both O and Cl atoms. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
