Pinonic Acid

The Reactions Of Ozone With Organic Compounds

“…In general, oxidations with silver oxide and peracetic acid give the least and the greatest amounts, respectively, of these products. "Abnormal" products reported by these and other authors wrere 2-8 per cent valeric acid and 0.8-1.2 per cent butyric acid from 6-dodecene (607), 4.7 per cent glutaric and 1.8 per cent succinic acid by the liquid-phase ozonolysis (607) and 10 per cent formic acid by the vapor-phase ozonolysis (244) of cyclohexene, 13-30 per cent of a mixture of 5-decanol (CLXIX) and 5-decanone and 1-7 per cent of acids with four to six carbon atoms from 3-butyl-l-octene (CLXVII) (607), small amounts of levulinic acid (CLXXIII, apparently by decarboxylation of CLXXII) (607), succinic acid (607), and /3-carboxyglutaric acid (CLXXIV) (395) from vinylcyclohexene (CLXXI), and pinononic acid (CLXXVI) (528) and pinic acid (CLXXVII) (262,311) from -pinene (CLXXV). It is apparent that these substances have resulted not only from rearrangement but also from oxidation of either "normal" or rearrangement products.…”

“…If the reactant readily absorbs ozone the completion of the reaction becomes apparent w'hen iodine is released in a potassium iodide trap following the ozonation vessel (591). The deterioration of natural rubber tubing attached to the ozonolysis vessel likewise indicates that ozone is in the effluent gas (262). A blue color of the cold ( -50°C.…”

alpha-Pinene, a starting material for a sequence of organic experiments

“…These are separated by filtration. Better yields and a cleaner product are obtained by ozonolysis of the a-pinene (32)(33)(34) in acetic acid or oxidation with peroxides (35). Many reactions of pinonic acid (XX) have been mentioned (6).…”