NOVEL CYCLIZATION TO BENZOFURANS IN THE REACTION OF ALKYNYL(P-PHENYLENE)BISIODONIUM DITRIFLATES WITH PHENOXIDE ANION

被引:30
作者
KITAMURA, T [1 ]
ZHENG, L [1 ]
TANIGUCHI, H [1 ]
SAKURAI, M [1 ]
TANAKA, R [1 ]
机构
[1] FUKUOKA UNIV,FAC ENGN,DEPT CHEM ENGN,FUKUOKA 81401,JAPAN
关键词
D O I
10.1016/S0040-4039(00)60614-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of alkynyl(p-phenylene)bisiodonium ditriflates (2) with sodium phenoxide in methanol provides 2-substituted benzofurans (3). This result indicates that beta-phenoxyalkylidenecarbenes generated by the reaction with phenoxide anion undergo novel intramolecular aromatic C-H insertion to afford benzofurans.
引用
收藏
页码:4055 / 4058
页数:4
相关论文
共 32 条
[1]  
[Anonymous], REV HETEROATOM CHEM
[2]  
[Anonymous], CHEM HALIDES PSEUDOH
[3]   SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE [J].
BACHI, MD ;
BARNER, N ;
CRITTELL, CM ;
STANG, PJ ;
WILLIAMSON, BL .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3912-3915
[4]   ACETYLENIC AND ETHYLENIC IODONIUM SALTS AND THEIR REACTIONS WITH A CARBANION [J].
BERINGER, FM ;
GALTON, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06) :1930-&
[5]   NEW SYNTHESIS OF BENZO[B]FURANS BY SRN1 REACTION OF ORTHO-IODOANISOLE [J].
BEUGELMANS, R ;
GINSBURG, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :508-509
[6]  
BUCKLE DR, 1985, J CHEM SOC P1, P2243
[7]  
FISHER DR, 1992, SYNLETT, P535
[8]   ACYLOXYALKYLIDENEPHOSPHORANES .3. STUDY OF OMEGA-ACYLOXYBENZYLIDENETRIPHENYLPHOSPHORANES - A NEW ROUTE TO BENZOFURANS [J].
HERCOUET, A ;
LECORRE, M .
TETRAHEDRON, 1981, 37 (16) :2867-2873
[9]   NOVEL ALKYNYL-SUBSTITUTED (P-PHENYLENE)BISIODONIUM DITRIFLATES - PREPARATION AND REACTION WITH THIOCYANATE ION [J].
KITAMURA, T ;
FURUKI, R ;
ZHENG, L ;
FUJIMOTO, T ;
TANIGUCHI, H .
CHEMISTRY LETTERS, 1992, (11) :2241-2244
[10]   GENERATION, TRAPPING AND FATE OF ALKYLIDENECARBENE-IODONIUM YLIDES FROM THE ADDITION OF NAN3 TO ALKYNYLPHENYLIODONIUM TOSYLATES [J].
KITAMURA, T ;
STANG, PJ .
TETRAHEDRON LETTERS, 1988, 29 (16) :1887-1890