N-HYDROXYPYRIDINE-2-THIONE CARBAMATES .7. INTERMOLECULAR ADDITION AND ADDITION-CYCLIZATION REACTIONS OF AMINIUM CATION RADICALS

被引:48
作者
NEWCOMB, M
KUMAR, MU
机构
[1] Department of Chemistry, Texas A and M University, College Station
关键词
D O I
10.1016/S0040-4039(00)88851-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dialkylaminium cation radicals produced from the title precursors add to ethyl vinyl ether to give β-amino ethers in good yields. When an allyl group is present on nitrogen, a cyclization reaction follows the addition, and pyrrolidines are formed. Simple cyclic enol ethers also can be employed. © 1990.
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页码:1675 / 1678
页数:4
相关论文
共 12 条
[1]   THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON, 1985, 41 (19) :3901-3924
[2]  
CHOW YL, 1971, TETRAHEDRON LETT, P1545
[3]   ATOM TRANSFER CYCLOADDITION - A FACILE PREPARATION OF FUNCTIONALIZED (METHYLENE)CYCLOPENTANES [J].
CURRAN, DP ;
CHEN, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6558-6560
[4]   REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].
ELAMIN, B ;
ANANTHARAMAIAH, GM ;
ROYER, GP ;
MEANS, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444
[5]  
Minisci F, 1976, Top Curr Chem, V62, P1
[6]  
NEALE RS, 1971, SYNTH-INT J METHODS, P1
[7]   FACILE GENERATION OF DIALKYLAMINYL RADICALS FROM N-HYDROXYPYRIDINE-2-THIONE CARBAMATES - APPLICATION IN KINETIC-STUDIES OF SMALL RING CYCLOALKYLAMINYL RADICAL RING OPENINGS [J].
NEWCOMB, M ;
PARK, SU ;
KAPLAN, J ;
MARQUARDT, DJ .
TETRAHEDRON LETTERS, 1985, 26 (46) :5651-5654
[8]   N-HYDROXYPYRIDINE-2-THIONE CARBAMATES AS AMINYL AND AMINIUM RADICAL PRECURSORS - CYCLIZATIONS FOR SYNTHESIS OF THE PYRROLIDINE NUCLEUS [J].
NEWCOMB, M ;
DEEB, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (10) :3163-3165
[9]  
NEWCOMB M, 1990, TETRAHEDRON, V46
[10]   A MILD GENERAL-METHOD FOR THE SYNTHESIS OF ALPHA-LINKED DISACCHARIDES [J].
REDDY, GV ;
KULKARNI, VR ;
MEREYALA, HB .
TETRAHEDRON LETTERS, 1989, 30 (32) :4283-4286