Trioxane

Trioxane refers to any of three isomeric organic compounds composed of a six-membered ring with three carbon atoms and three oxygen atoms, having the molecular formula C₃H₆O₃.

Trioxane isomers:1,2,3-trioxane (left), 1,2,4-trioxane (middle), and 1,3,5-trioxane (right)

The three isomers are:

1,2,3-trioxane, a hypothetical compound related to molozonide,[1]
1,2,4-trioxane, a hypothetical compound whose skeleton occurs as a structural element of some antimalarial agents (artemisinin and similar drugs),[2]
1,3,5-trioxane, a trimer of formaldehyde used as fuel and in plastics manufacture, and also as a solid fuel tablet when combined with Hexamine.

References

Lay, Tsan H.; Yamada, Takahiro; Tsai, Po-Lun; Bozzelli, Joseph W. (1997). "Thermodynamic Parameters and Group Additivity Ring Corrections for Three- to Six-Membered Oxygen Heterocyclic Hydrocarbons". Journal of Physical Chemistry A. 101 (13): 2471–2477. doi:10.1021/jp9629497.
Gary H. Posner, Mikhail Krasavin, Michael McCutchen, Poonsakdi Ploypradith, John P. Maxwell, Jeffrey S. Elias, Michael H. Parker (2001). "New antimalarial trioxanes and endoperoxides". Antimalarial Chemotherapy: 255–263.CS1 maint: multiple names: authors list (link)

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[1] Lay, Tsan H.; Yamada, Takahiro; Tsai, Po-Lun; Bozzelli, Joseph W. (1997). "Thermodynamic Parameters and Group Additivity Ring Corrections for Three- to Six-Membered Oxygen Heterocyclic Hydrocarbons". Journal of Physical Chemistry A. 101 (13): 2471–2477. doi:10.1021/jp9629497.

[2] Gary H. Posner, Mikhail Krasavin, Michael McCutchen, Poonsakdi Ploypradith, John P. Maxwell, Jeffrey S. Elias, Michael H. Parker (2001). "New antimalarial trioxanes and endoperoxides". Antimalarial Chemotherapy: 255–263.CS1 maint: multiple names: authors list (link)