Über den Abbau von Cumaronen und Thionaphthen durch Ozon

The Reactions Of Ozone With Organic Compounds

“…Ozonolysis of benzofuran (CCCLIIa) gave salicyclic acid (CCCLIIIa) (25 per cent), salicylaldehyde (CCCLIIIb) (40 per cent), and catechol (CCCLIIIc) (10 per cent) (560). Similar results were obtained with 2-methyland 3-methylbenzofurans and 3,7-dimethylbenzofuran (560). Likewise, benzothiophene (CCCLIIb) was converted to CCCLIVa (30 per cent), CCCLIVb (20 per cent), and CCCLIVc (50 per cent) (560).…”

“…Similar results were obtained with 2-methyland 3-methylbenzofurans and 3,7-dimethylbenzofuran (560). Likewise, benzothiophene (CCCLIIb) was converted to CCCLIVa (30 per cent), CCCLIVb (20 per cent), and CCCLIVc (50 per cent) (560). In these cases oxidation of the ) in 24 per cent yield and a stable monoozonide (m.p.…”

“…Oxidation of aldehydes is known to give by-products of lower carbon content (364,526,527,558,559,560,607). Thus, during the ozonolysis of CLXVII, CLXIX and 5-decanone could have arisen both from rearrangement of zwitterion CLXVIII and by oxidation of CLXX, the normal ozonolysis product.…”

Cleavages and Rearrangements Involving Oxygen Radicals and Cations.

“…Furthermore, the yields of phenols from aldehydes are lower than the yields of phenols from the corresponding cinnamic esters under comparable conditions (58). Hydrogenation rather than hydrolysis of the ozonide does not prevent the formation of abnormal products (69,75).…”

“…Oleic acid ozonide has also been used as a reagent for the conversion of suitably substituted benzaldehydes to the corresponding phenols (69). Rieche (55) has shown that a decomposing ozonide gives some -hydroxyhydroperoxide and that the latter can give up hydrogen peroxide to other carbonyl compounds.…”