Singlet oxygen with sodium hypochlorite

Excited singlet oxygen generated in situ by oxidising hydrogen peroxide with sodium hypochlorite, produces results chemically indistinguishable from photo-sensitised auto-oxidation of olefins [70]. 

HH Nknz and G Turznik. Reactions of Lignin with Singlet Oxygen. I. Oxidation of Monomeric and Dimeric Model Compounds with Sodium Hypochlorite Hydrogen Peroxide. Cell Chem Technol 14 727-742, 1980. 

Foote, Wexler, and Ando 92) showed that, in the oxidation of unsaturated hydrocarbons with oxygen in the anglet state (which may be produced by electrodeless discharge 93) or by reaction of HgOs with sodium hypochlorite), the same products are formed as in the photosensitized oxidation. Kawaoka, Khan and Kearns 94 reviewed the data reported in the literature, which support the formation of singlet Og by quenching excited triplet state molecules. 

Recently, a clever approach was used by Foote and Wexler (1964a, b) which further substantiates the excitation transfer mechanism. The chemiluminescence produced upon reaction of hydrogen peroxide with sodium hypochlorite in aqueous solution has been, tentatively, identified as phosphorescence from a low-lying singlet state of molecular oxygen (Khan and Kasha, 1963, 1964). In preliminary studies, Foote and Wexler (1964a, b) have shown that the species produced from this thermal reaction in the presence of several substrates yields the same products as are formed in the photosensitized oxidations, e.g., Eqs. (174)-(176). 

Singlet oxygen can be produced chemically as well as by photochemical sensitization. There are several chemical methods available, one of the best known being the reaction of sodium hypochlorite with peroxide ... 

Conjugated dienes (and compounds that behave like conjugated dienes in the Diels-Alder reaction) react with singlet oxygen to form cyclic peroxides as if molecular oxygen acted as a dienophile. The yields of the peroxides, prepared by photochemical oxidation [13, 55] or by chemical oxidations with hydrogen peroxide and sodium hypochlorite, alkaline hydrogen peroxide and bromine, alkaline salts of peroxy acids [14, 26], or the ozonide of triphenyl phosphite [29], are comparable. 

Singlet oxygen 102(I g) is obtained by reacting active chlorine contained in sodium and calcium hypochlorites with hydrogen peroxide [Refs. 20, 23, 26, 108,109, 222, 223]... 

Sodium hypochlorite hydrogen peroxide Oxidations with singlet oxygen Ethyleneperoxides from 1,3-dienes... 

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