Comparative autoxidation of 3-Carene and α-Pinene: Factors governing regioselective hydrogen abstraction reactions

Gadi Rothenberg; Yael Yatziv; Yoel Sasson

doi:10.1016/S0040-4020(97)10319-2

Comparative autoxidation of 3-Carene and α-Pinene: Factors governing regioselective hydrogen abstraction reactions

Gadi Rothenberg
, Yael Yatziv
, Yoel Sasson^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

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 6 as the major product.

Original language	English
Pages (from-to)	593-598
Number of pages	6
Journal	Tetrahedron
Volume	54
Issue number	3-4
DOIs	https://doi.org/10.1016/S0040-4020(97)10319-2
State	Published - 15 Jan 1998

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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 6 as the major product.",

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N2 - 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 6 as the major product.

AB - 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 6 as the major product.

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Comparative autoxidation of 3-Carene and α-Pinene: Factors governing regioselective hydrogen abstraction reactions

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