FREE-RADICAL CYCLIZATIONS OF TERMINAL ALKYNES WITH OXIME ETHERS

被引：58
作者：
ENHOLM, EJ
BURROFF, JA
JARAMILLO, LM
机构：
[1] Department of Chemistry, University of Florida, Gainesville
来源：
TETRAHEDRON LETTERS | 1990年 / 31卷 / 26期
关键词：
D O I：
10.1016/S0040-4039(00)97455-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A benzyl oxime ether tethered to a terminal alkyne efficiently undergoes a free radical hydrostannylation reaction to afford five- and six-membered rings bearing a protected amine and a vinyl stannane functionality. These products were subsequently protiodestannylated to obtain the unsubstituted exo-methylene compounds. © 1990.
引用
收藏
页码：3727 / 3730
页数：4
相关论文
共 15 条
[1]   RADICAL CYCLIZATION OF OXIME ETHERS [J].
BARTLETT, PA ;
MCLAREN, KL ;
TING, PC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1633-1634
[2]   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
[3]  
CURRAN DP, 1988, SYNTHESIS-STUTTGART, V417, P489
[4]  
GIESE B, 1986, ORADICALS ORGANIC SY
[5]   FREE-RADICAL CARBON-CARBON BOND FORMATION IN ORGANIC-SYNTHESIS [J].
HART, DJ .
SCIENCE, 1984, 223 (4639) :883-887
[6]   BIS(TRIMETHYLSTANNYL)BENZOPINACOLATE-MEDIATED INTERMOLECULAR FREE-RADICAL CARBON CARBON BOND-FORMING REACTIONS - A NEW ONE-CARBON HOMOLOGATION [J].
HART, DJ ;
SEELY, FL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1631-1633
[7]  
NEUMANN WP, 1987, SYNTHESIS-STUTTGART, P665
[8]   SEQUENTIAL RADICAL CYCLIZATION, ALKOXY RADICAL FRAGMENTATION, AND RECYCLIZATION PROCESSES - A NOVEL METHOD FOR THE SYNTHESIS OF FUSED CYCLOHEPTANONES AND CYCLOOCTENONES FROM CYCLOHEXANONES [J].
NISHIDA, A ;
TAKAHASHI, H ;
TAKEDA, H ;
TAKADA, N ;
YONEMITSU, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) :902-904
[9]  
Pereyre M., 1987, TIN ORGANIC SYNTHESI
[10]   RADICAL REACTIONS IN ORGANIC-SYNTHESIS [J].
RAMAIAH, M .
TETRAHEDRON, 1987, 43 (16) :3541-3676
12