Experimental and theoretical study on the reactivity of the R-CN/H2O2 system in the epoxidation of unfunctionalized olefins

被引：13

作者：

von Holleben, MLA ^{[1
]}

Livotto, PR ^{[1
]}

Schuch, CM ^{[1
]}

机构：

[1] Univ Fed Rio Grande Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2001年 / 12卷 / 01期

关键词：

epoxidation; alkenes; peroxycarboximidic acid;

D O I：

10.1590/S0103-50532001000100005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study on the reactivity of peroxycarboximidic acids in situ generated from acetonitrile, trichloroacetonitrile, benzonitrile, m-chlorobenzonitrile, 3-cyanopyridine, 1-naphthonitrile and 9-anthracenenitrile was performed by semiempirical AM1 method and experimentally in the epoxidation of cyclohexene and R-(+)-limonene. Experimental results showed that the reactivity of Cl3CCN/H2O2 was quite similar to MCPBA in the epoxidation of unfunctionalized olefins when a biphasic mixture CH2Cl2/H2O was employed as solvent.

引用

页码：42 / 46

页数：5

共 18 条

[1] EPOXIDATION OF ALKENES WITH TRICHLOROACETONITRILE HYDROGEN-PEROXIDE IN A NEUTRAL BIPHASIC SOLVENT SYSTEM [J].

ARIAS, LA ;

ADKINS, S ;

NAGEL, CJ ;

BACH, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :888-890

[2] A hydrogen-bonded model for the syn epoxidation of cyclic allylic ethers under Payne conditions [J].

Bachmann, C ;

Gesson, JP ;

Renoux, B ;

Tranoy, I .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :379-382

[3] EPOXIDATION .3. RELATIVE REACTIVITIES OF SOME REPRESENTATIVE OLEFINS WITH PEROXYBENZIMIDIC ACID [J].

CARLSON, RG ;

BEHN, NS ;

COWLES, C .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (24) :3832-&

[4] THE DIASTEREOMERIC 8,9-EPOXIDES OF LIMONENE (THE 8,9-EPOXY-PARA-MENTH-1-ENES) [J].

CARMAN, RM ;

DEVOSS, JJ ;

GREENFIELD, KL .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (03) :441-446

[5] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[6] A THEORETICAL INVESTIGATION OF THE STRUCTURE AND ROTATIONAL BARRIERS OF PEROXYFORMIMIDIC ACID - THE MECHANISM OF STEREOMUTATION AT THE CARBON-NITROGEN DOUBLE-BOND [J].

LANG, TJ ;

WOLBER, GJ ;

BACH, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (12) :3275-3282

[7]

MCISAAC JJE, 1961, J ORG CHEM, V36, P3048

[8] A SIMPLIFIED PROCEDURE FOR EPOXIDATION BY BENZONITRILE-HYDROGEN PEROXIDE - SELECTIVE OXIDATION OF 2-ALLYLCYCLOHEXANONE [J].

PAYNE, GB .

TETRAHEDRON, 1962, 18 (JUN) :763-&

[9] REACTIONS OF HYDROGEN PEROXIDE .7. ALKALI-CATALYZED EPOXIDATION AND OXIDATION USING A NITRILE AS CO-REACTANT [J].

PAYNE, GB ;

WILLIAMS, PH ;

DEMING, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (03) :659-&

[10] REACTIONS OF HYDROGEN PEROXIDE .6. ALKALINE EPOXIDATION OF ACRYLONITRILE [J].

PAYNE, GB ;

WILLIAMS, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (03) :651-&

← 1 2 →