User:Benjah-bmm27/Diphosphorus tetraiodide
From Wikipedia, the free encyclopedia
| Diphosphorus tetraiodide | |
|---|---|
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| IUPAC name | Diphosphorus tetraiodide |
| Other names | phosphorus(II) iodide |
| Identifiers | |
| CAS number | [13455-00-0] |
| Properties | |
| Molecular formula | P2I4 |
| Molar mass | 569.57 g mol−1 |
| Appearance | orange crystalline solid |
| Density | ? g cm−3, solid |
| Melting point |
124-127 °C |
| Boiling point |
Decomposes |
| Solubility in water | Decomposes |
| Hazards | |
| EU classification | not listed |
| Flash point | non-flammable |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Diphosphorus tetraiodide, P2I4, is an orange crystalline solid, and a versatile reducing agent.
Contents |
[edit] Synthesis
Diphosphorus tetraiodide is easily generated by the disproportionation of phosphorus triiodide in dry ether:
- 2PI3 → P2I4 + I2
It can also be obtained by reacting phosphorus trichloride and potassium iodide in anhydrous conditions[1].
[edit] Reactions
P2I4 reacts with bromine to form a mixture of PI3, PBr3, PBr2I and PBrI2[2].
[edit] Applications
Diphosphorus tetraiodide is used in organic chemistry for converting carboxylic acids to nitriles[3], for deprotecting acetals and ketals to aldehydes and ketones, and for converting epoxides into alkenes and aldoximes into nitriles. It can also cyclize 2-aminoalcohols to aziridines[4] and to convert α,β-unsaturated carboxylic acids to α,β-unsaturated bromides[5].
[edit] References
- ^ H. Suzuki, T. Fuchita, A. Iwasa, T. Mishina (December 1978). "Diphosphorus Tetraiodide as a Reagent for Converting Epoxides into Olefins, and Aldoximes into Nitriles under Mild Conditions". Synthesis (12): 905-908. doi:.
- ^ A. H. Cowley and S. T. Cohen (June 1965). "The Iodides of Phosphorus. II. The Reaction of Bromine with Diphosphorus Tetraiodide". Tetrahedron Letters 4 (8): 1221-1222. doi:.
- ^ Vikas N. Telvekar and Rajesh A. Rane (August 2007). "A novel system for the synthesis of nitriles from carboxylic acids". Tetrahedron Letters 48 (34): 6051-6053. doi:.
- ^ H. Suzuki, H. Tani (1984). "A mild cyclization of 2-aminoalcohols to aziridines using diphosphorus tetraiodide". Chemistry Letters 13 (12): 2129-2130. doi:.
- ^ Vikas N. Telvekar, Somsundaram N. Chettiar (June 2007). "A novel system for decarboxylative bromination". Tetrahedron Letters 48 (26): 4529-4532. doi:.
