The thermodynamic and kinetic stabilities of several novel substituted trioxanes have been explored computationally. Our calculations show that concerted ring opening provides the most likely path for dissociation to the building block molecules: CO2, CH2O, and CCl2O. These studies indicate that gem-dichlorotrioxane (C3H4O3Cl2, 1), tetrachlorotrioxane (C3H2O3Cl4, 7), and trioxanone (C3H4O4, 2) should be kinetically stable and are likely candidates for synthesis.