PREPARATION OF 6 MEMBERED CARBOCYCLES BY ARYL-TELLURIUM MEDIATED FREE-RADICAL CYCLIZATION

被引:27
作者
BARTON, DHR [1 ]
DALKO, PI [1 ]
GERO, SD [1 ]
机构
[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/S0040-4039(00)92289-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Radical cyclisation of various telluro-compounds was examined. Olefins conjugated to an electron withdrawing group, (7, 8, 9, 10, and 11) gave high yields of the corresponding six membered products. Non-activated olefin 23 gave the corresponding thiopyridyl derivative 24 as the only product. The photolysis, using oxime 18 as radicophile for the cyclisation, proceeded slowly at room temperature, and gave only a low yield of products 19 and 20.
引用
收藏
页码:4713 / 4716
页数:4
相关论文
共 18 条
[1]   SYNTHESIS OF BIOLOGICALLY-ACTIVE CARBOCYCLIC ANALOGS OF N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE (MDP) [J].
BARTON, DHR ;
CAMARA, J ;
DALKO, P ;
GERO, SD ;
QUICLETSIRE, B ;
STUTZ, P .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3764-3766
[2]   GENERATION AND FATE OF NONDECARBOXYLATING ACYLOXY RADICALS DERIVED FROM THE PHOTOLYSIS OF ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE [J].
BARTON, DHR ;
RAMESH, M .
TETRAHEDRON LETTERS, 1990, 31 (07) :949-952
[3]  
BARTON DHR, 1990, TETRAHEDRON, V46, P215
[4]   SYNTHETIC METHODS FOR THE PREPARATION OF D-PSEUDO-SUGARS AND L-PSEUDO-SUGARS FROM D-GLUCOSE [J].
BARTON, DHR ;
GERO, SD ;
CLEOPHAX, J ;
MACHADO, AS ;
QUICLETSIRE, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (17) :1184-1186
[5]   TANDEM NUCLEOPHILIC AND RADICAL CHEMISTRY IN THE REPLACEMENT OF THE HYDROXYL GROUP BY A CARBON CARBON BOND - A CONCISE SYNTHESIS OF SHOWDOMYCIN [J].
BARTON, DHR ;
RAMESH, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :891-892
[6]   TELLURIUM IN ORGANIC-CHEMISTRY .1. NOVEL SYNTHESIS OF BIARYLS [J].
BERGMAN, J .
TETRAHEDRON, 1972, 28 (12) :3323-&
[7]   RADICAL REACTIONS AND RETROSYNTHETIC PLANNING [J].
CURRAN, DP .
SYNLETT, 1991, (02) :63-72
[8]   CATALYTIC DEBROMINATION OF VICINAL DIBROMIDES [J].
ENGMAN, L .
TETRAHEDRON LETTERS, 1982, 23 (35) :3601-3602
[9]   A GENERAL-APPROACH TO CARBOCYCLIC SUGAR ANALOGS - PREPARATION OF A CARBOCYCLIC ANALOG OF BETA-D-FRUCTOFURANOSE [J].
GAUDINO, JJ ;
WILCOX, CS .
CARBOHYDRATE RESEARCH, 1990, 206 (02) :233-250
[10]   METHODS IN CHALCOGEN CHEMISTRY .5. NEW REAGENT FOR SYNTHESIS OF AROMATIC TELLURIUM COMPOUNDS [J].
GUNTHER, WHH ;
NEPYWODA, J ;
CHU, JYC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 74 (01) :79-84