Mn(III)-induced molecular oxygen trapping reaction of alkenes with 2,3-pyrrolidinedione derivatives. A novel entry to 1-hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonan-9-ones

被引：30

作者：

Nguyen, VH

Nishino, H

Kurosawa, K

机构：

[1] KUMAMOTO UNIV,FAC SCI,DEPT CHEM,KUMAMOTO 860,JAPAN

[2] KUMAMOTO UNIV,GRAD SCH SCI & TECHNOL,DEPT ENVIRONM SCI,KUMAMOTO 860,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)00166-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular oxygen trapping reaction of alkenes with 2,3-pyrrolidinedione derivatives was developed using a Mn(III)-induced oxidation system. Alkenes and 2,3-pyrrolidinediones were treated with manganese(III) acetate in acetic acid under a stream of dry air, giving 1-hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonan-9-ones in good yields. The reaction involved molecular oxygen trapping of radicals which were formed by the addition of pyrrolidinedione radicals induced by Mn(III) to alkenes. (C) 1997 Elsevier Science Ltd.

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页码：1773 / 1776

页数：4

相关论文

共 29 条

[11] Convenient synthesis of 3-cyano-4,5-dihydrofurans and 4-cyano-1,2-dioxan-3-ols using acylacetonitrile building block [J].

Nguyen, VH ;

Nishino, H ;

Kurosawa, K .

TETRAHEDRON LETTERS, 1996, 37 (28) :4949-4952

[12] Formation of tetrahydrofuran derivatives and acetonylation of alkenes using carbon radicals derived from manganese(III) oxidation of diketene [J].

Nishino, H ;

Nguyen, VH ;

Yoshinaga, S ;

Kurosawa, K .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8264-8271

[13] MANGANESE(III)-MEDIATED CARBON CARBON BOND FORMATION IN THE REACTION OF XANTHENES WITH ACTIVE METHYLENE-COMPOUNDS [J].

NISHINO, H ;

KAMACHI, H ;

BABA, H ;

KUROSAWA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3551-3557

[14] THE FACILE SYNTHESIS OF DIHYDROFURANS BY THE OXIDATION OF OLEFINS WITH TRIS(2,4-PENTANEDIONATO)MANGANESE(III) [J].

NISHINO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (07) :1922-1927

[15]

NISHINO H, 1990, B CHEM SOC JPN, V64, P1800

[16] Reaction of oligomethylene di(3-oxobutanoate) with 1,1-disubstituted alkenes and molecular oxygen in the presence of manganese(II and or III) acetate [J].

Ouyang, J ;

Nishino, H ;

Kurosawa, K .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (06) :1783-1792

[17]

Ouyang J, 1996, J HETEROCYCLIC CHEM, V33, P1291

[18] ANTIFUNGAL PEROXIDE-CONTAINING ACIDS FROM 2 CARIBBEAN SPONGES [J].

PHILLIPSON, DW ;

RINEHART, KL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7735-7736

[19] SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS BY THE ACID-CATALYZED DECOMPOSITION OF 1,2-DIOXAN-3-OLS [J].

QIAN, CY ;

HIROSE, J ;

NISHINO, H ;

KUROSAWA, K .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (05) :1219-1227

[20] MANGANESE(II AND III)-MEDIATED SYNTHESIS OF CYCLIC PEROXIDES FROM ALKENES, ACTIVE METHYLENE-COMPOUNDS, AND MOLECULAR-OXYGEN [J].

QIAN, CY ;

YAMADA, T ;

NISHINO, H ;

KUROSAWA, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (05) :1371-1378