Reactions of P4S10 and pyPS2Cl with N,N′-diphenylurea and N,N′-diphenylthiourea

The reaction of P4S10 (1) with N,N′-diphenylurea (PhNH)2CO (2) results in new heterocyclic compounds: the pyridinium salt of 1,3-diphenyl-2-sulfido-2-thioxo-1,3-diaza-2λ5-phosphetidine (3) (with a P–N–C–N cycle) and the pyridinium salt of 1,4-diphenyl-2,5-disulfido-2,5-dithioxo-1,4-dithiadiaza-2λ5,5λ5-diphosphinane (4), containing the (P–S–N)2 cycle and the cyclic thiophosphates [pyH]2[P2S8] (5), [pyH]2[P2S7] (6) and [pyH]3[P3S9] (7). A similar reaction, but carried out with N,N′-diphenylthiourea (PhNH)2CS (8), leads to the formation of 4 and 6. pyPS2Cl (9), used as an alternative starting material, also yields compounds 3, 4, 5, and further [pyH][PS2Cl2] (10) and S8 after reaction with 2. Compound 3 reacts with Pd(CH3COO)2, with the formation of the complex [Pd(Ph2N2COPS2)2] (11). The crystal structures of 3 and 7 were determined by single-crystal X-ray diffraction.

Two new heterocyclic compounds, the pyridinium salts of 1,3-diphenyl-2-sulfido-2-thioxo-1,3-diaza-2λ5-phosphetidine (with a P–N–C–N cycle) and 1,4-diphenyl-2,5-disulfido-2,5-dithioxo-1,4-dithiadiaza-2λ5,5λ5-diphosphinane (containing a (P–S–N)2 cycle), were prepared in the reaction of P4S10 with N,N′-diphenylurea (PhNH)2CO (2). The cyclic thiophosphates [pyH]2[P2S8], [pyH]2[P2S7] and [pyH]3[P3S9] were also formed.Figure optionsDownload as PowerPoint slide