Selective fries rearrangement catalyzed by zinc powder

被引：20

作者：

Paul, S ^{[1
]}

Gupta, M ^{[1
]}

机构：

[1] Univ Jammu, Dept Chem, Jammu 180006, India

来源：

SYNTHESIS-STUTTGART | 2004年 / 11期

关键词：

acetylated phenols; zinc powder; Fries rearrangement; microwave activation; selectivity;

D O I：

10.1055/s-2004-829152

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Zinc powder in the presence of N,N-dimethylformamide efficiently catalyzes the selective Fries rearrangement of acetylated phenols under microwave heating or with conventional heating using an oil bath. In some cases different products were obtained using microwave heating and conventional heating. Selective migration of the acyl group has been noted with good yields.

引用

页码：1789 / 1792

页数：4

共 29 条

[1] Synthesis of o-arylenedizinc compounds from 1-iodo-2-trifluoromethylsulfonyloxybenzenes and zinc powder and their synthetic application
Amano, M
Saiga, A
Ikegami, R
Ogata, T
Takagi, K
[J]. TETRAHEDRON LETTERS, 1998, 39 (47) : 8667 - 8668
[2] MICROWAVE-ASSISTED ORGANIC-REACTIONS
CADDICK, S
[J]. TETRAHEDRON, 1995, 51 (38) : 10403 - 10432
[3] Zinc mediated transesterification of β-ketoesters and coumarin synthesis
Chavan, SP
Shivasankar, K
Sivappa, R
Kale, R
[J]. TETRAHEDRON LETTERS, 2002, 43 (47) : 8583 - 8586
[4] Genuinely catalytic Fries rearrangement using sulfated zirconia
Clark, JH
Dekamin, MG
Moghaddam, FM
[J]. GREEN CHEMISTRY, 2002, 4 (04) : 366 - 368
[5] CLARK JH, 1994, CATALYSIS ORGANIC RE, P41
[6] de la Hoz A, 2000, EUR J ORG CHEM, V2000, P3659
[7] GUISNET M, 2001, FINE CHEM HETEROGENE, P211
[8] Fries rearrangement in ionic melts
Harjani, JR
Nara, SJ
Salunkhe, MM
[J]. TETRAHEDRON LETTERS, 2001, 42 (10) : 1979 - 1981
[9] Highly selective Fries rearrangement over zeolites and Nafion in silica composite catalysts: A comparison
Heidekum, A
Harmer, MA
Hoelderich, WF
[J]. JOURNAL OF CATALYSIS, 1998, 176 (01) : 260 - 263
[10] Zinc-metal promoted selective α-haloacylation and gem-bisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane
Ishino, Y
Mihara, M
Takeuchi, T
Takemoto, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3503 - 3506

← 1 2 3 →