A two-component pericyclic reaction for synthesis of substituted benzofurans and aryl-quaternary carbon bonds

被引:20
作者
Hendrickson, JB [1 ]
Walker, MA [1 ]
机构
[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA
关键词
D O I
10.1021/ol000113n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction shown is presumed to be a new [3,3]-sigmatropic rearrangement involving an O-arylsulfoxonium species or related sulfurane, It allows a sulfoxide and a phenol to be joined and rearranged in one operation at or below room temperature, coupling an aromatic to a quaternary carbon and creating benzofurans or articulated dihydrobenzofurans in a number of examples. [Graphics]
引用
收藏
页码:2729 / 2731
页数:3
相关论文
共 19 条
[1]   LEWIS ACID-PROMOTED 3-AZA-COPE REARRANGEMENT OF N-ALKYL-N-ALLYLANILINES [J].
BEHOLZ, LG ;
STILLE, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5095-5100
[2]   ENE-TYPE ADDITION OF ALKENES TO PHENYL VINYLSULFOXIDE [J].
BRICHARD, MH ;
JANOUSEK, Z ;
MERENYI, R ;
VIEHE, HG .
TETRAHEDRON LETTERS, 1992, 33 (18) :2511-2514
[3]   ACID-CATALYZED REACTIONS OF PHENOLS WITH DIMETHYL SULFOXIDE AND DICYCLOHEXYLCARBODIIMIDE [J].
BURDON, MG ;
MOFFATT, JG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (20) :4656-&
[4]  
Burgstahler A.W., 1973, Org. Synth.Coll, V5, P251
[5]   ADDITIVE PUMMERER REACTIONS OF VINYLIC SULFOXIDES - SYNTHESIS OF GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED ESTERS AND ALPHA-HYDROXYKETONES [J].
CRAIG, D ;
DANIELS, K ;
MACKENZIE, AR .
TETRAHEDRON LETTERS, 1990, 31 (44) :6441-6444
[6]   SYNTHETIC FUROCOUMARINS . XANTHOTOXIN AND METHYLXANTHOTOXINS [J].
DESOUZA, NJ ;
NAYAK, PV ;
SECCO, E .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1966, 3 (01) :42-&
[7]   EXCLUSIVE ORTHO SUBSTITUTION OF PHENOLS VIA [2,3]-SIGMATROPIC REARRANGEMENTS [J].
GASSMAN, PG ;
AMICK, DR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7611-7619
[8]   VARIETY OF THERMAL PERICYCLIC REACTIONS [J].
HENDRICKSON, JB .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (01) :47-76
[9]  
HENDRICKSON JB, 1995, J CHEM INF COMP SCI, V35, P852
[10]  
LABIAD B, 1989, SYNTHESIS-STUTTGART, P143