Mechanism of oxygen transfer in the epoxidation of an olefin by molecular oxygen in the presence of an aldehyde

被引：36

作者：

Jarboe, SG ^{[1
]}

Beak, P ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 03期

关键词：

D O I：

10.1021/ol991304x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The reaction pathway for peroxide-initiated aldehyde-mediated oxidation of olefins to epoxides by molecular oxygen has been studied. The pathways of reaction via a peroxy acid or an acyl peroxy radical have been differentiated by investigation of the reaction of 4 with oxygen to provide 6 via 8.

引用

收藏

页码：357 / 360

页数：4

相关论文

共 16 条

[1]

[Anonymous], 1976, RUSS CHEM REV+, DOI DOI 10.1070/RC1976V045N02ABEH002618

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] A practical decarboxylative hydroxylation of carboxylic acids [J].

Barton, DHR ;

Géro, SD ;

Holliday, P ;

Quiclet-Sire, B ;

Zard, SZ .

TETRAHEDRON, 1998, 54 (24) :6751-6756

[4] DETERMINATIONS OF TRANSITION-STATE GEOMETRIES BY THE ENDOCYCLIC RESTRICTION TEST - MECHANISMS OF SUBSTITUTION AT NONSTEREOGENIC ATOMS [J].

BEAK, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (05) :215-222

[5]

Filippova TY, 1982, RUSS CHEM REV, V51, P582, DOI DOI 10.1070/RC1982V051N06ABEH002867

[6]

GROENOEWEGEN P, 1978, TETRAHEDRON LETT, V5, P491

[7] METAL-DEPENDENT REACTIVITY OF SOME METALLOPORPHYRINS IN OXIDATION WITH DIOXYGEN [J].

HABER, J ;

MLODNICKA, T ;

POLTOWICZ, J .

JOURNAL OF MOLECULAR CATALYSIS, 1989, 54 (03) :451-461

[8] Comparison of gas phase and condensed phase SNi reactions.: The competitive four-and five-centre cyclisations of the 3,4-epoxybutoxide anion.: A joint experimental and theoretical study [J].

Hevko, JM ;

Dua, S ;

Taylor, MS ;

Bowie, JH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (07) :1629-1634

[9] A CONVENIENT SYNTHESIS OF EPOXIDES FROM OLEFINS USING MOLECULAR-OXYGEN IN THE ABSENCE OF METAL-CATALYSTS [J].

KANEDA, K ;

HARUNA, S ;

IMANAKA, T ;

HAMAMOTO, M ;

NISHIYAMA, Y ;

ISHII, Y .

TETRAHEDRON LETTERS, 1992, 33 (45) :6827-6830

[10]

MARTIN JC, 1968, ADV CHEM SER, V75, P269