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Triphenyl phosphite ozonide

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Triphenyl phosphite ozonide
Names
IUPAC name 4,4,4-triphenoxy-1,2,3,45-trioxaphosphetane
Identifiers
CAS Number
3D model (JSmol)
Abbreviations TPPO
PubChem CID
InChI
  • InChI=1S/C18H15O6P/c1-4-10-16(11-5-1)19-25(23-22-24-25,20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15HKey: BVCCTQHXJQXLKM-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)OP2(OOO2)(OC3=CC=CC=C3)OC4=CC=CC=C4
Properties
Chemical formula C18H15O6P
Molar mass 358.286 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Triphenyl phosphite ozonide (TPPO) is a chemical compound with the formula PO3(C6H5O)3 that is used to generate singlet oxygen.

When TPPO is mixed with amines, the ozonide breaks down into singlet oxygen and leaves behind triphenyl phosphite. Pyridine is the only known amine that can effectively cause the breakdown of TPPO while not quenching any of the produced oxygen.

Synthesis

Triphenyl phosphite ozonide is created by bubbling dry ozone through dichloromethane with triphenyl phosphite being added dropwise at -78 °C. If triphenyl phosphite is added in excess in the synthesis, TPPO can be reduced to triphenyl phosphite oxide, PO(C6H5O)3, and oxygen gas.

References

  1. ^ Pryor, William A.; Govindan, C. K. (November 1981). "Decomposition of triphenyl phosphite ozonide in the presence of spin traps". The Journal of Organic Chemistry. 46 (23): 4679–4682. doi:10.1021/jo00336a010. ISSN 0022-3263.
  2. ^ Bartlett, Paul D.; Mendenhall, G. David; Durham, Dana L. (October 1980). "Controlled generation of singlet oxygen at low temperatures from triphenyl phosphite ozonide". The Journal of Organic Chemistry. 45 (22): 4269–4271. doi:10.1021/jo01310a001. ISSN 0022-3263.
  3. Mendenhall, G. David; Priddy, Duane B. (1999-08-01). "A Reexamination of the Ozone−Triphenyl Phosphite System. The Origin of Triphenyl Phosphate at Low Temperatures". The Journal of Organic Chemistry. 64 (16): 5783–5786. doi:10.1021/jo982339y. ISSN 0022-3263.


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