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Phosphorus–nitrogen compounds. Part 20: Fully substituted spiro-cyclotriphosphazenic lariat (PNP-pivot) ether derivatives

2010; Elsevier BV; Volume: 76; Issue: 3-4 Linguagem: Inglês

10.1016/j.saa.2010.04.007

1873-3557

Aytuğ Okumuş, S. Bilge, Zeynel Kılıç, Aslı Öztürk, Tuncer Hökelek, Filiz Yılmaz,

Synthesis of Organic Compounds

The condensation reactions of partly substituted spiro-cyclotriphosphazenic lariat (PNP-pivot) ethers, N3P3[(o-NHPhO)2R]Cl4 [where R = –CH2CH2– (1) and –CH2CH2OCH2CH2– (2)] with morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) produce fully substituted morpholino (3 and 4) and 1,4-dioxa-8-azaspiro[4,5]deca (5 and 6) phosphazenes. These are the new examples of the spiro-cyclophosphazenic lariat ether derivatives with N2Ox (x = 2 and 3) donor type containing 11- and 14-membered macrocycles. The solid state structures of 3, 5 and 6 have been determined by X-ray diffraction techniques. Compound 3 has intermolecular N–H…O hydrogen bond, compound 5 has intra- and intermolecular N–H…O hydrogen bonds, while compound 6 has intramolecular N–H…O and O–H…N and intermolecular N–H…O and O–H…O hydrogen bonds. The correlations of the endocyclic (α) and exocyclic (α′) NPN bond angles with δPspiro values are investigated. The structural investigations of 3–6 have been verified by elemental analyses, MS, FTIR, 1H, 13C and 31P NMR, DEPT and HETCOR techniques.