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

被引：56

作者：

Rothenberg, G ^{[1
]}

Yatziv, Y ^{[1
]}

Sasson, Y ^{[1
]}

机构：

[1] Hebrew Univ Jerusalem, Casali Inst Appl Chem, IL-91904 Jerusalem, Israel

来源：

TETRAHEDRON | 1998年 / 54卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4020(97)10319-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Autoxidation reactions of 3-Carene 1 and alpha-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. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：593 / 598

页数：6

共 39 条

[1] NMR-SPECTRA AND CONFORMATIONS OF CYCLIC COMPOUNDS .8. CAR-3-ENE [J].

ABRAHAM, RJ ;

COOPER, MA ;

WHITTAKER, D .

ORGANIC MAGNETIC RESONANCE, 1973, 5 (11) :515-516

[2] ALLYLIC OXIDATION OF OLEFINS CATALYZED BY COBALT CHLORIDE - THE BENEFICIAL EFFECT OF N-METHYLPYRROLIDINONE [J].

ALPER, H ;

HARUSTIAK, M .

JOURNAL OF MOLECULAR CATALYSIS, 1993, 84 (01) :87-92

[3] CHEMISTRY OF TERPENES .20. AUTOXIDATION OF (+)-CAR-3-ENE [J].

BAINES, DA ;

COCKER, W .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22) :2232-2237

[4] COPPER-CATALYSED REACTIONS OF TERT-BUTYL PERBENZOATE WITH CIS-PARA-MENTH-2-ENE AND TRANS-PARA-MENTH-2-ENE AND OTHER CYCLIC OLEFINS [J].

BECKWITH, ALJ ;

PHILLIPOU, G .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (06) :1277-1294

[5] C-13 NMR-SPECTRA OF MONOTERPENES [J].

BOHLMANN, F ;

ZEISBERG, R ;

KLEIN, E .

ORGANIC MAGNETIC RESONANCE, 1975, 7 (09) :426-432

[6] KINETIC STUDIES IN THE CHEMISTRY OF RUBBER AND RELATED MATERIALS .7. INFLUENCE OF CHEMICAL STRUCTURE ON THE ALPHA-METHYLENIC REACTIVITY OF OLEFINS [J].

BOLLAND, JL .

TRANSACTIONS OF THE FARADAY SOCIETY, 1950, 46 (4-5) :358-368

[7] DIRECTIVE EFFECTS IN ATTACK OF PHENYL RADICALS ON CARBON-HYDROGEN BONDS [J].

BRIDGER, RF ;

RUSSELL, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (23) :3754-&

[8] CONFORMATIONAL EFFECTS IN FREE-RADICAL HYDROGEN ABSTRACTION FROM MEDIUM-RING CYCLOALKANES [J].

BUNCE, NJ ;

HADLEY, M .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2271-2276

[9] PALLADIUM-CATALYZED ALLYLIC OXIDATION OF CYCLOHEXENES USING MOLECULAR-OXYGEN AS OXIDANT [J].

BYSTROM, SE ;

LARSSON, EM ;

AKERMARK, B .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5674-5675

[10] STUDIES RELATING TO THE OXIDATIVE-DEGRADATION OF NATURAL-RUBBER - THE AUTOXIDATION OF 1-METHYLCYCLOHEXENE - PRIMARY PRODUCT ANALYSIS, ALLYLIC HYDROPEROXIDE ISOLATION, AND REGIOCHEMISTRY OF THE INITIAL EVENTS [J].

COURTNEIDGE, JL ;

BUSH, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) :1227-1229

← 1 2 3 4 →