Abstract
The reaction with oxygen of cyanisopropyl free radicals generated by the polymerization catalyst 2,2′-azobisisobutyronitrile has been investigated. In xylene, or benzene, as solvent at 55° the products identified are: (1) a new compound, 2-cyano-2-propyl hydroperoxide; (2) acetone cyanohydrin; (3) hydrogen cyanide; (4) cyanogen; (5) acetone; (6) p-methyl benzaldehyde (in xylene only); and (7) tetramethylsuccinodinitrile. The hydroperoxide is surprisingly stable; its physical constants are: b.p. 37 °C at 1 mm Hg; m.p. −9 to −8°; [Formula: see text] 1.4138; d20 1.013 g/ml. In benzene under the same experimental conditions, only a very small amount of the hydroperoxide is obtained, the principal product being acetone cyanohydrin. A free-radical mechanism is proposed. The induced decomposition of the hydroperoxide, which is important in benzene, is almost completely inhibited in the presence of xylene. The new hydroperoxide can be used as a polymerization catalyst at moderately elevated temperatures.
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