Palladium-catalyzed oxidation of monoterpenes: novel tandem oxidative coupling-oxidation of camphene by dioxygen

被引：40

作者：

da Silva, MJ ^{[1
]}

Gusevskaya, EV ^{[1
]}

机构：

[1] Univ Fed Minas Gerais, Dept Quim, ICEX, BR-31270901 Belo Horizonte, MG, Brazil

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2001年 / 176卷 / 1-2期

关键词：

palladium; monoterpenes; oxidative couplings; oxidation;

D O I：

10.1016/S1381-1169(01)00240-0

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The Pd-catalyzed stereoselective oxidative coupling of (-)-camphene gives mainly (E,E)-diene, i.e., bis(3,3-dimethyl-2-norbornylidene)ethane, which can be oxidized into the corresponding alpha,beta -unsaturated ketone, i.e. (3,3-dimethyl-2-norbornyl) (8-camphenyl)ketone, with LiNO3 being used as a reoxidant and dioxygen as a final oxidant; these two reactions are performed in a one port process with up to 90% selectivity for ketone. The applications of the Pd(II)/NO3- catalytic system to the oxidation of limonene and beta -pinene have also been studied. (C) 2001 Elsevier Science B.V. All rights reserved.

引用

页码：23 / 27

页数：5

共 19 条

[1] THE TRANSITION-METAL NITRO-NITROSYL REDOX COUPLE - CATALYTIC-OXIDATION OF OLEFINS TO KETONES [J].

ANDREWS, MA ;

KELLY, KP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (10) :2894-2896

[2] A NEW APPROACH TO THE AIR OXIDATION OF ALKENES EMPLOYING METAL NITRO COMPLEXES AS CATALYSTS [J].

ANDREWS, MA ;

CHANG, TCT ;

CHENG, CWF ;

KELLY, KP .

ORGANOMETALLICS, 1984, 3 (12) :1777-1785

[3] NITRO AND NITRATO PALLADIUM COMPLEXES IN OXIDATION PROCESSES - THE MECHANISM OF THE FORMATION OF 1,1-ADDITION AND 1,2-ADDITION PRODUCTS DURING ETHYLENE OXIDATION IN CHLOROFORM ACETIC-ACID SOLUTION [J].

BECK, IE ;

GUSEVSKAYA, EV ;

STEPANOV, AG ;

LIKHOLOBOV, VA .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 73 (02) :115-146

[4] OXYGEN-TRANSFER REACTIONS CATALYZED BY NITROPALLADIUM(II) COMPLEXES - REACTIVITY OF BIS(MU-CHLORO)BIS[EXO-3-(NITROSOOXY)BICYCLO[2.2.1]-HEPT-2-YL-C,N]DIPALLADIUM - CLEAVAGE OF THE C-PD BOND [J].

CHAUVET, F ;

HEUMANN, A ;

WAEGELL, B .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (10) :1916-1922

[5]

DIAS AO, 1997, TETRAHEDRON LETT, V31, P41

[6] Selective palladium-catalysed functionalization of limonene: synthetic and mechanistic aspects [J].

El Firdoussi, L ;

Baqqa, A ;

Allaoud, S ;

Allal, BA ;

Karim, A ;

Castanet, Y ;

Mortreux, A .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 135 (01) :11-22

[7] ACETOXYLATION AND METHOXYLATION OF TERPENE OLEFINS CATALYZED BY PALLADIUM(II) [J].

ELFIRDOUSSI, L ;

BENHARREF, A ;

ALLAOUD, S ;

KARIM, A ;

CASTANET, Y ;

MORTREUX, A ;

PETIT, F .

JOURNAL OF MOLECULAR CATALYSIS, 1992, 72 (02) :L1-L5

[8] Palladium(II) catalyzed oxidation of naturally occurring terpenes with dioxygen [J].

Gusevskaya, E ;

Gonsalves, JA .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1997, 121 (2-3) :131-137

[9] Palladium-catalyzed oxidation of bicyclic monoterpenes by hydrogen peroxide [J].

Gusevskaya, E ;

Robles-Dutenhefner, PA ;

Ferreira, VMS .

APPLIED CATALYSIS A-GENERAL, 1998, 174 (1-2) :177-186

[10] Platinum/tin catalyzed hydroformylation of naturally occurring monoterpenes [J].

Gusevskaya, EV ;

dos Santos, EN ;

Augusti, R ;

Dias, AD ;

Foca, CM .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 152 (1-2) :15-24

← 1 2 →