PREPARATION, MOLECULAR-STRUCTURE, AND DIELS-ALDER CYCLOADDITION CHEMISTRY OF BETA-FUNCTIONALIZED ALKYNYL(PHENYL)IODONIUM SALTS

被引:67
作者
WILLIAMSON, BL [1 ]
STANG, PJ [1 ]
ARIF, AM [1 ]
机构
[1] UNIV UTAH,DEPT CHEM,SALT LAKE CITY,UT 84112
关键词
D O I
10.1021/ja00060a007
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A variety of functionalized alkynyliodonium salts 4a-o are prepared in good yields via a novel iodonium-transfer process between the appropriate alkynylstannanes 2 and PhI+CN.-OTf. The electron-deficient acetylenes 4 readily undergo cycloaddition reactions at room temperature with endocyclic. exocyclic,and acyclic 1,3-dienes to afford functionalized vinyliodonium adducts of type 5, 6, 7, and 9.
引用
收藏
页码:2590 / 2597
页数:8
相关论文
共 64 条
[11]   ABINITIO INVESTIGATIONS OF THE BETA-SILICON EFFECT ON ALKYL AND CYCLOPROPYL CARBENIUM IONS AND RADICALS [J].
IBRAHIM, MR ;
JORGENSEN, WL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :819-824
[13]   AMINO-DERIVATIVES OF METALS AND METALLOIDS .I. PREPARATION OF AMINOSTANNANES STANNYLAMINES AND STANNAZANES [J].
JONES, K ;
LAPPERT, MF .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1944-&
[14]   IMPROVED SYNTHESIS OF ALKYNYLPHENYLIODONIUM ARYLSULFONATES (RC=CIPH.OSO2AR) [J].
KITAMURA, T ;
STANG, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4105-4106
[15]   SELECTIVE COUPLING REACTIONS OF ALKYNYL(PHENYL)IODONIUM TOSYLATES WITH ALKYNYLCOPPER REAGENTS [J].
KITAMURA, T ;
TANAKA, T ;
TANIGUCHI, H ;
STANG, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2892-2893
[16]  
KLEINER FG, 1968, LIEBIGS ANN CHEM, V716, P19
[17]   FUNCTIONALIZATION OF ALKENES AND ALKYNES WITH [HYDROXY(TOSYLOXY)IODO]BENZENE - BIS(TOSYLOXY)ALKANES, VINYLARYLIODONIUM TOSYLATES, AND ALKYNYLARYLIODONIUM TOSYLATES [J].
KOSER, GF ;
REBROVIC, L ;
WETTACH, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (21) :4324-4326
[18]   INTERACTION OF THE CARBON-TIN BOND WITH BETA-POSITIVE CHARGE [J].
LAMBERT, JB ;
WANG, GT .
TETRAHEDRON LETTERS, 1988, 29 (21) :2551-2554
[19]   THE BETA-EFFECT OF SILICON IN THE SYNPERIPLANAR GEOMETRY [J].
LAMBERT, JB ;
CHELIUS, EC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8120-8126
[20]   INTERACTION OF THE CARBON-GERMANIUM OR CARBON TIN BOND WITH POSITIVE CHARGE ON A BETA-CARBON [J].
LAMBERT, JB ;
WANG, GT ;
TERAMURA, DH .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5422-5428