Spontaneous decomposition, peroxidic compounds

This is one of the rare cases of spontaneous generation of a peroxide bond from oxygen fragments. The structure of 35 is confirmed by IR and NMR spectra. The F19-NMR spectrum shows that the compound exists mainly in the tram form. The cis compound is less stable than the trans isomer, more than 50% of the cis isomer having decomposed within 3 days, whereas the tram isomer had not decomposed. The decomposition of 35 yields difluorocarbene. 

Contact with readily oxidizable substances may produce spontaneous combustion. Concentrated solutions can detonate on heating. The rate of decomposition increases by 1.5 times for every — 12°C (10°F) increase in temperature (NFPA 1997). Mixing with organic compounds may cause violent explosions. This includes alcohols, acetone and other ketones, aldehydes, carboxylic acids, and their anhydrides. With acetic acid and acetic anhydride, peroxyacetic acid is formed. In the presence of excessive anhydride, diacetyl peroxide is formed. Both the peroxy acids and the organic peroxides are shock-sensitive explosive compounds. Spontaneous ignition occurs when added to cotton (cellulose). 

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