CERIUM(IV) AMMONIUM-NITRATE PROMOTED OXIDATIVE CYCLIZATION OF DIMETHYL 4-PENTENYLMALONATE

被引:27
作者
BACIOCCHI, E [1 ]
PAOLOBELLI, AB [1 ]
RUZZICONI, R [1 ]
机构
[1] UNIV PERUGIA,DIPARTIMENTO CHIM,I-06100 PERUGIA,ITALY
关键词
CERIUM(IV) AMMONIUM NITRATE; FREE RADICAL CYCLIZATION; ELECTROPHILIC 5-HEXENYL RADICALS;
D O I
10.1016/S0040-4020(01)81235-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
CAN promoted oxidative cyclization of dimethyl 4-pentenylmonate has been investigated in MeOH and in AcOH. The product distribution and the regioselectivity of the reaction (5-exo/6-endo ratio) appear to be very sensitive to the reaction conditions as well as to the presence and the nature of copper salts, which can also be exploited from the synthetic point of view.
引用
收藏
页码:4617 / 4622
页数:6
相关论文
共 14 条
[1]   ELECTRONIC AND STERIC EFFECTS IN THE ADDITION OF ELECTROPHILIC 1,3-DICARBONYLALKYL RADICALS TO STYRENES [J].
BACIOCCHI, E ;
RUZZICONI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4772-4778
[2]  
BACIOCCHI E, 1989, NATO ADV SCI I C-MAT, V260, P155
[3]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[4]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].
BECKWITH, ALJ .
TETRAHEDRON, 1981, 37 (18) :3073-3100
[5]   CYCLIZATIONS OF UNSATURATED.CR(COX)2 RADICALS - MANGANESE(III) ACETATE OXIDATIVE CYCLIZATIONS OF UNSATURATED ACETOACETATES AND ATOM-TRANSFER CYCLIZATIONS OF UNSATURATED HALOACETOACETATES GIVE THE SAME RADICALS [J].
CURRAN, DP ;
MORGAN, TM ;
SCHWARTZ, CE ;
SNIDER, BB ;
DOMBROSKI, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6607-6617
[6]   ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].
CURRAN, DP ;
CHANG, CT .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157
[7]  
CURRAN DP, 1988, SYNTHESIS-STUTTGART, V417, P489
[8]  
GIESE B, 1986, RADICALS ORGANIC SYN, pCH4
[9]   FREE-RADICAL CARBON-CARBON BOND FORMATION IN ORGANIC-SYNTHESIS [J].
HART, DJ .
SCIENCE, 1984, 223 (4639) :883-887
[10]   FREE-RADICAL CYCLIZATIONS [J].
JULIA, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (11) :386-&