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
收藏
页码：821 / 824
页数：4
相关论文
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 [J].
BRISCOE, MW ;
CHAMBERS, RD ;
MULLINS, SJ ;
NAKAMURA, T ;
VAUGHAN, JFS ;
DRAKESMITH, FG .
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 [J].
BUTTLE, LA ;
MOTHERWELL, WB .
TETRAHEDRON LETTERS, 1994, 35 (23) :3995-3998
[6]   FLUORINATED DI-ENES [J].
CHAMBERS, RD ;
VAUGHAN, JFS ;
MULLINS, SJ ;
NAKAMURA, T ;
ROCHE, AJ .
JOURNAL OF FLUORINE CHEMISTRY, 1995, 72 (02) :231-233
[7]   REACTIONS INVOLVING FLUORIDE-ION .40. AMINES AS INITIATORS OF FLUORIDE-ION CATALYZED-REACTIONS [J].
CHAMBERS, RD ;
GRAY, WK ;
KORN, SR .
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+) [J].
Fox, JR ;
Foxman, BM ;
Guarrera, D ;
Miller, JS ;
Calabrese, JC ;
Reis, AH .
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 [J].
ITOH, T ;
OHARA, H ;
EMOTO, S .
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 [J].
MEDEBIELLE, M .
TETRAHEDRON LETTERS, 1995, 36 (12) :2071-2074
12