INTRAMOLECULAR ADDITION OF VINYL AND ARYL RADICALS TO OXIME ETHERS IN THE SYNTHESIS OF 5-MEMBERED, 6-MEMBERED AND 7-MEMBERED RING-SYSTEMS

被引:73
作者
BOOTH, SE
JENKINS, PR
SWAIN, CJ
SWEENEY, JB
机构
[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,LEICS,ENGLAND
[2] MERCK SHARP & DOHME LTD,HARLOW CM20 2QR,ESSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 23期
关键词
D O I
10.1039/p19940003499
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxime ethers 2a-e have been cyclised with Bu(3)SnH to the alkoxyamino-3-methylidene-chromanes 3a-e. Seven-membered ring formation was observed when the oxime ethers 7a, b were converted into the dibenzo [b,e] oxepines 8a, b under similar conditions. 1-Methoxyaminoindanes 12a, b were produced from the cyclisation of the substrates 11a, b and the cis-fused cyclic products 15a, b and 18 were obtained from compounds 14a, b and 17, respectively.
引用
收藏
页码:3499 / 3508
页数:10
相关论文
共 29 条
[1]   X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .24. PREPARATION AND THERMAL FRAGMENTATION OF IMIDAZOLIDINES - INFLUENCE OF METAL-SALTS ON PYRROLIDINE VERSUS IMIDAZOLIDINE FORMATION [J].
AMORNRAKSA, K ;
BARR, D ;
DONEGAN, G ;
GRIGG, R ;
RATANANUKUL, P ;
SRIDHARAN, V .
TETRAHEDRON, 1989, 45 (14) :4649-4668
[2]   FREE-RADICAL CYCLIZATION APPROACH TO THE SOUTHERN MOIETY OF AVERMECTINS [J].
ARDISSON, J ;
FEREZOU, JP ;
JULIA, M ;
PANCRAZI, A .
TETRAHEDRON LETTERS, 1987, 28 (18) :2001-2004
[3]   RADICAL CYCLIZATION OF OXIME ETHERS [J].
BARTLETT, PA ;
MCLAREN, KL ;
TING, PC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1633-1634
[4]  
BARTON DHR, 1992, J CHEM SOC P1, P2471
[5]   THE SYNTHESIS OF BICYCLIC AND TRICYCLIC RING-SYSTEMS BY RADICAL CYCLIZATION REACTIONS OF OXIME ETHERS [J].
BOOTH, SE ;
JENKINS, PR ;
SWAIN, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1248-1249
[6]   HEATS OF COMBUSTION AND STRAIN ENERGIES OF BICYCLO N.M.0!ALKANES [J].
CHANG, S ;
BOYD, RH ;
MCNALLY, D ;
SHARYTEH.S ;
HICKEY, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3109-&
[7]   LITHIUM-HALOGEN EXCHANGE-INITIATED CYCLIZATION REACTIONS .3. INTRAMOLECULAR CONJUGATE ADDITION-REACTIONS OF UNSATURATED ACYLPHOSPHORANES [J].
COOKE, MP ;
WIDENER, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1381-1396
[8]   CYCLIC POLYOLEFINS .7. STRUCTURE OF THE 8-MEMBERED CYCLIC DIMER OF CHLOROPRENE [J].
COPE, AC ;
SCHMITZ, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (07) :3056-3062
[9]   CONVERSION OF KETONES HAVING DELTA,EPSILON-PI-FUNCTIONS TO CYCLOPENTANOLS BY ZINC-TRIMETHYLCHLOROSILANE [J].
COREY, EJ ;
PYNE, SG .
TETRAHEDRON LETTERS, 1983, 24 (28) :2821-2824
[10]  
ELIEL EL, 1962, STEREOCHEMISTRY CARB, P273