Formation of 1,2-dioxolanes using Mn(III)-based reaction of various arylacetylenes with 2,4-pentanedione and related reaction

被引：21

作者：

Tsubusaki, Takuma ^{[1
]}

Nishino, Hiroshi ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Sci & Technol, Dept Chem, Kumamoto 8608555, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 18期

基金：

日本学术振兴会;

关键词：

1,2-Dioxolane; Cyclic peroxides; Manganese(III) acetate; Aerobic oxidation; Oxirane; FREE-RADICAL CYCLIZATIONS; MANGANESE(III) ACETATE; MOLECULAR-OXYGEN; CYCLIC PEROXIDES; VINYL RADICALS; STEREOSELECTIVE-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; ARTEMISININ DERIVATIVES; AMMONIUM-NITRATE; SIMPLE ROUTE;

D O I：

10.1016/j.tet.2009.02.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The manganese(III)-based aerobic oxidation of arylacetylenes with 2,4-pentanedione at ambient temperature unexpectedly gave the 1,2-dioxolane derivatives in moderate yields together with a small amount of the oxiranes. The 1,2-dioxolanes underwent silica gel-assisted contraction to quantitatively give the oxiranes. The reaction pathway for the formation of the 1,2-dioxolanes and the by-product was discussed. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3745 / 3752

页数：8

共 29 条

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[12] Mn(III)-based reaction of alkenes with pyrrolidinedione derivatives. Formation of bicyclic peroxides and the related compounds
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[15] FORMATION OF 1,2-DIOXACYCLOHEXANES BY THE REACTION OF ALKENES WITH TRIS(2,4-PENTANEDIONATO)MANGANESE(III) OR WITH BETA-KETOCARBONYL COMPOUNDS IN THE PRESENCE OF MANGANESE(III) ACETATE
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[20] Highly diastereoselective formation of 3,7-dioxabicyclo[3.3.0]octan-2-ones in reaction of 2-arylcyclopropanedicarboxylates with aromatic aldehydes using 1,2-zwitterionic reactivity type
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