Triphenyl phosphite ozonide
Names
IUPAC name
4,4,4-triphenoxy-1,2,3,4λ5-trioxaphosphetane
Identifiers
3D model (JSmol)
Abbreviations TPPO
  • 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/h1-15H
    Key: BVCCTQHXJQXLKM-UHFFFAOYSA-N
  • C1=CC=C(C=C1)OP2(OOO2)(OC3=CC=CC=C3)OC4=CC=CC=C4
Properties
C18H15O6P
Molar mass 358.286 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triphenyl phosphite ozonide (TPPO) is a chemical compound with the formula PO3(C6H5O)3 that is used to generate singlet oxygen.[1][2]

When TPPO is mixed with amines, the ozonide breaks down into singlet oxygen and leaves behind triphenyl phosphite.[2] Pyridine is the only known amine that can effectively cause the breakdown of TPPO while not quenching any of the produced oxygen.[1][2]

Synthesis

Triphenyl phosphite ozonide is created by bubbling dry ozone through dichloromethane with triphenyl phosphite being added dropwise at -78 °C.[2] If triphenyl phosphite is added in excess in the synthesis, TPPO can be reduced to triphenyl phosphite oxide, PO(C6H5O)3, and oxygen gas.[3]

References

  1. 1 2 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. 1 2 3 4 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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