Reaction of the 2(bromodifluoromethyl)benzoxazole with tetrakis(dimethylamino)ethylene (TDAE) in the presence of aldehydes. A convenient synthesis of 2-(difluoromethyl)benzoxazole alcohols.

被引：28

作者：

Burkholder, C

Dolbier, WR

Medebielle, M

机构：

[1] UNIV DENIS DIDEROT,ELECTROCHIM MOL LAB,CNRS,F-75251 PARIS 05,FRANCE

[2] UNIV FLORIDA,DEPT CHEM,GAINESVILLE,FL 32611

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(96)02440-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of the 2-(bromodifluoromethyl)benzoxazole 1. The generated 2-(difluorormethyl) benzoxazole anion was trapped with several aldehydes 2-9, under mild conditions, to give the corresponding 2-(difluoromethyl)benzoxazole alcohols 10-17, in moderate to good yields. (C) 1997, Published by Elsevier Science Ltd.

引用

页码：821 / 824

页数：4

共 16 条

[1] [Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2] BOCK H, 1984, ANGEW CHEM INT EDIT, V233, P305
[3] REACTIONS INVOLVING FLUORIDE-ION .38. NEW FLUORINATED DIENES BY DEFLUORINATION
BRISCOE, MW
CHAMBERS, RD
MULLINS, SJ
NAKAMURA, T
VAUGHAN, JFS
DRAKESMITH, FG
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21): : 3115 - 3118
[4] BURKHOLDER C, UNPUB
[5] COMPARATIVE-STUDIES ON THE GENERATION AND CYCLIZATION REACTIONS OF DIFLUOROALKYL RADICALS
BUTTLE, LA
MOTHERWELL, WB
[J]. TETRAHEDRON LETTERS, 1994, 35 (23) : 3995 - 3998
[6] FLUORINATED DI-ENES
CHAMBERS, RD
VAUGHAN, JFS
MULLINS, SJ
NAKAMURA, T
ROCHE, AJ
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1995, 72 (02) : 231 - 233
[7] REACTIONS INVOLVING FLUORIDE-ION .40. AMINES AS INITIATORS OF FLUORIDE-ION CATALYZED-REACTIONS
CHAMBERS, RD
GRAY, WK
KORN, SR
[J]. TETRAHEDRON, 1995, 51 (48) : 13167 - 13176
[8] Characterization of novel TCNQ and TCNE 1:1 and 1:2 salts of the tetrakis(dimethyamino)ethylene dication, [{(CH3)(2)N}C-2-C{N(CH3)(2)}(2)](2+)
Fox, JR
Foxman, BM
Guarrera, D
Miller, JS
Calabrese, JC
Reis, AH
[J]. JOURNAL OF MATERIALS CHEMISTRY, 1996, 6 (10) : 1627 - 1631
[9] SYNTHESIS OF NEW ALPHA,ALPHA-DIFLUORO-GAMMA-LACTONES THROUGH INTRAMOLECULAR RADICAL CYCLIZATION AS A KEY REACTION
ITOH, T
OHARA, H
EMOTO, S
[J]. TETRAHEDRON LETTERS, 1995, 36 (20) : 3531 - 3534
[10] ELECTROCHEMICAL ADDITION OF CHLORODIFLUOROACETYL AROMATIC-COMPOUNDS TO ELECTRON-RICH OLEFINIC SUBSTRATES - A CONVENIENT SYNTHESIS OF GEM-DIFLUORO HETEROCYCLIC-COMPOUNDS
MEDEBIELLE, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (12) : 2071 - 2074

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