Trimethylolpropane phosphite
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Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.[1]
Preparation and reactions
It is prepared by reaction of trimethylolpropane with phosphorus trichloride or by transesterification with trimethylphosphite:[2]
- P(OMe)3 + EtC(CH2OH)3 → 3 MeOH + EtC(CH2O)3P
The first member of this series was derived from trimethylolethane,[3] but these derivatives are often poorly soluble. For this reason, the ethyl derivative has received more attention.[4]
Reactions
The compound forms an isolable ozonide, which degrades above 0 °C to release singlet O2.[1]
Coordination chemistry
Several EtCage complexes are known, since the ligand is highly basic (for a phosphite) and has a small ligand cone angle (101°). Illustrative complexes include [(EtCage)2Mo(CO)4], [Ir4(CO)11(EtCage)] and (CpMe5)RuCl(EtCage)2, shown below.
Ball-and-stick model of the bis(trimethylolpropane phosphite)molybdenum tetracarbonyl complex Ball-and-stick model of the (trimethylolpropane phosphite)tetrairidium undecacarbonyl cluster File:(CpMe5)RuCl(EtCage)2-from-xtal-1996-3D-balls.png
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Safety
Trimethylolpropane phosphite is very toxic and is a convulsant. LD50 is 1.1 mg per kg bodyweight (mice, i.p.).[5][6]
References
- ↑ a b Script error: No such module "citation/CS1".
- ↑ Verkade, J. G. "Spectroscopic studies of metal-phosphorus bonding in coordination complexes" Coordination Chemistry Reviews 1972, vol. 9, 1-106. Script error: No such module "CS1 identifiers".
- ↑ Verkade, J. G.; Reynolds, L. T. "The synthesis of a novel ester of phosphorus and of arsenic" Journal of Organic Chemistry (1960), 25, 663-5. Script error: No such module "CS1 identifiers".
- ↑ Huttemann, T. J., Jr.; Foxman, B. M.; Sperati, C. R.; Verkade, J. G. "Transition metal complexes of a constrained phosphite ester. IV. Compounds of cobalt(I), cobalt(III), nickel(II), and nickel(0)" Inorganic Chemistry (1965), 4(7), 950-3. Script error: No such module "CS1 identifiers".
- ↑ Ralf Stöhr et al. Chemische Kampfstoffe und Schutz vor chemischen Kampfstoffen 2. Aufl. Militärverlag der DDR, 1985 (german)
- ↑ Script error: No such module "Citation/CS1".
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