FACILE SYNTHESIS OF DIHYDROFURANS BY THE CERIUM(IV) AMMONIUM-NITRATE MEDIATED OXIDATIVE ADDITION OF 1,3-DICARBONYL COMPOUNDS TO CYCLIC AND ACYCLIC ALKENES - RELATIVE SUPERIORITY OVER THE MANGANESE(III) ACETATE MEDIATED PROCESS

被引:70
作者
NAIR, V
MATHEW, J
机构
[1] Organic Chemistry Division, Regional Research Laboratory (CSIR)
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 03期
关键词
D O I
10.1039/p19950000187
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radicals generated from dimedone and acetylacetone by CAN undergo addition to cyclic and acyclic alkenes to give dihydrofurans in good yields. In view of the experimental simplicity and higher yields of products formed CAN appears to be superior to the more commonly used Mn(OAc)(3).
引用
收藏
页码:187 / 188
页数:2
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共 22 条
[11]   OXIDATION BY METAL-SALTS .10. ONE-STEP SYNTHESIS OF GAMMA-LACTONES FROM OLEFINS [J].
HEIBA, EI ;
DESSAU, RM ;
RODEWALD, PG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :7977-7981
[12]  
HEIBA EI, 1971, J AM CHEM SOC, V93, P534
[13]   COBALT(II) ACETATE PROMOTED OXIDATIVE ADDITION OF 1,3-DICARBONYL COMPOUNDS TO ALKENES UNDER AEROBIC CONDITIONS [J].
IQBAL, J ;
BHATIA, B ;
NAYYAR, NK .
TETRAHEDRON, 1991, 47 (32) :6457-6468
[14]   TRANSITION METAL-PROMOTED FREE-RADICAL REACTIONS IN ORGANIC-SYNTHESIS - THE FORMATION OF CARBON-CARBON BONDS [J].
IQBAL, J ;
BHATIA, B ;
NAYYAR, NK .
CHEMICAL REVIEWS, 1994, 94 (02) :519-564
[15]   AROMATIC ACETONYLATION PROMOTED BY MANGANESE(III) AND CERIUM(IV) SALTS [J].
KURZ, ME ;
BARU, V ;
NGUYEN, PN .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1603-1607
[16]   FREE-RADICAL AROMATIC NITROMETHYLATION PROMOTED BY CERIUM(IV) [J].
KURZ, ME ;
NGOVIWATCHAI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4672-4676
[17]   MANGANESE(III) MEDIATED REACTIONS OF UNSATURATED SYSTEMS [J].
MELIKYAN, GG .
SYNTHESIS-STUTTGART, 1993, (09) :833-850
[18]   GAMMA-SELECTIVITY IN THE CERIC AMMONIUM-NITRATE PROMOTED OXIDATIVE ADDITION OF SILYL DIENOL ETHERS TO SILYL ENOL ETHERS [J].
PAOLOBELLI, AB ;
LATINI, D ;
RUZZICONI, R .
TETRAHEDRON LETTERS, 1993, 34 (04) :721-724
[19]   RADICAL REACTIONS IN ORGANIC-SYNTHESIS [J].
RAMAIAH, M .
TETRAHEDRON, 1987, 43 (16) :3541-3676
[20]   CYCLIZATION OF VINYL RADICALS - A NEW VERSATILE METHOD FOR THE CONSTRUCTION OF 5-MEMBERED AND 6-MEMBERED RINGS [J].
STORK, G ;
BAINE, NH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (08) :2321-2323