CYCLIZATIONS AND INTERMOLECULAR ADDITIONS OF ALKOXYCARBONYLOXY RADICALS FROM N-HYDROXYPYRIDINE-2-THIONE CARBONATES

被引:45
作者
NEWCOMB, M
KUMAR, MU
BOIVIN, J
CREPON, E
ZARD, SZ
机构
[1] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843
[2] ECOLE POLYTECH,SYNTH ORGAN LAB,F-91123 PALAISEAU,FRANCE
关键词
D O I
10.1016/S0040-4039(00)71214-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkoxycarbonyloxy radicals from allyl and homoallyl alcohols cyclize in an exo fashion to give, respectively, 3-substituted 1,2-diol carbonates and 4-substituted 1,3-diol carbonates whereas simple alkoxycarbonyloxy radicals add intermolecularly to ethyl vinyl ether to give, ultimately, carbonates of glycolaldehyde derivatives.
引用
收藏
页码:45 / 48
页数:4
相关论文
共 15 条
[1]  
Barton D. H. R., COMMUNICATION
[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]   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
[4]   GENERATION OF ALKOXY RADICALS FROM N-ALKOXYPYRIDINETHIONES [J].
BECKWITH, ALJ ;
HAY, BP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4415-4416
[5]  
BECKWITH ALJ, 1989, J AM CHEM SOC, V111, P240
[6]  
BECKWITH ALJ, 1980, REARRANGEMENTS GROUN, V1
[7]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (06) :417-439
[8]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (07) :489-513
[9]  
Giese B., 1986, RADICALS ORGANIC SYN
[10]   N-HYDROXYPYRIDINE-2-THIONE CARBAMATES .6. FUNCTIONALIZATION OF CARBON RADICALS FORMED BY AMINIUM CATION RADICAL CYCLIZATIONS [J].
NEWCOMB, M ;
MARQUARDT, DJ ;
KUMAR, MU .
TETRAHEDRON, 1990, 46 (07) :2345-2352