Tetrahedron

Comparative autoxidation of 3-carene and α-pinene: factors governing regioselective hydrogen abstraction reactions

G Rothenberg, Y Yatziv, Y Sasson

Index: Rothenberg, Gadi; Yatziv, Yael; Sasson, Yoel Tetrahedron, 1998 , vol. 54, # 3-4 p. 593 - 598

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Citation Number: 55

Abstract

Autoxidation reactions of 3-Carene 1 and α-Pinene 2 were performed using various homogeneous catalysts. Different product and regio-selectivities were observed. The factors that promote hydrogen abstraction (HA) reactions in both molecules are discussed, and it is proposed that the difference in the product selectivities is due to the lack of “cyclic activation” in 2. Oxidation of 1 produced mainly 3-carene-5-one 3, while 2 yielded 2, 3-epoxypinane ...