N-(ORTHO-ARYLOXYPHENYL)ARYLIMIDOYL RADICALS - NOVEL 1,5-ARYL RADICAL TRANSLOCATION FROM OXYGEN TO CARBON

被引:23
作者
GUIDOTTI, S [1 ]
LEARDINI, R [1 ]
NANNI, D [1 ]
PARESCHI, P [1 ]
ZANARDI, G [1 ]
机构
[1] UNIV BOLOGNA,DIPARTIMENTO CHIM ORGAN A MANGINI,I-40136 BOLOGNA,ITALY
关键词
D O I
10.1016/0040-4039(94)02283-H
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imidoyl radicals 4a-d, obtained by hydrogen abstraction from imines 1a-d, give 7-membered cyclisation leading to oxazapines 2a-d. The intermediate spirocyclohexadienyl radicals of the competitive 6-membered ring closure (6a-d) rearrange to aryloxy radicals, giving benzophenones 3a-d: the whole process entails a novel 1,5-aryl radical translocation from an oxygen to a carbon atom.
引用
收藏
页码:451 / 454
页数:4
相关论文
共 21 条
[1]   INTRAMOLECULAR ADDITION OF CARBON-CENTERED TINTHIOIMIDOYL RADICALS TO CARBON CARBON DOUBLE-BONDS - SYNTHESIS OF GAMMA-THIOLACTAMS AND DELTA-THIOLACTAMS [J].
BACHI, MD ;
DENENMARK, D .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3442-3444
[2]   CYCLIZATIONS OF ENE RADICALS - IMIDOYL RADICALS AS INTERMEDIATES IN THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].
BACHI, MD ;
DENENMARK, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1886-1888
[3]   FREE-RADICAL ADDITION OF ALKANETHIOLS TO ALKYNES - REARRANGEMENTS OF THE INTERMEDIATE BETA-THIOVINYL RADICALS [J].
BENATI, L ;
CAPELLA, L ;
MONTEVECCHI, PC ;
SPAGNOLO, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2818-2823
[4]  
CANTAREL R, 1960, B SOC CHIM FR, P362
[5]   TIN RADICAL-ADDITION TO ALKYNYL SULFIDES - REACTIVITY OF THE INTERMEDIATE THIOALKYL-SUBSTITUTED BETA-(TRIBUTYLSTANNYL)VINYL RADICALS [J].
CAPELLA, L ;
MONTEVECCHI, PC ;
NANNI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3368-3374
[6]   1ST SPECTROSCOPIC AND ABSOLUTE KINETIC-STUDIES ON (ALKOXYCARBONYL)OXYL RADICALS AND AN UNSUCCESSFUL ATTEMPT TO OBSERVE CARBAMOYLOXYL RADICALS [J].
CHATEAUNEUF, J ;
LUSZTYK, J ;
MAILLARD, B ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6727-6731
[7]   4+1 RADICAL ANNULATIONS WITH ISONITRILES - A SIMPLE ROUTE TO CYCLOPENTA-FUSED QUINOLINES [J].
CURRAN, DP ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2127-2132
[8]   ON THE NEOPHYL-LIKE REARRANGEMENT OF 2-(9-ANTHRYL)ETHYL RADICALS [J].
LEARDINI, R ;
NANNI, D ;
PEDULLI, GF ;
TUNDO, A ;
ZANARDI, G ;
FORESTI, E ;
PALMIERI, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :7723-7732
[9]   THE REACTION OF (2-ALKYLIDENAMINOPHENYL)SULFIDES WITH DI-ISO-PROPYL PEROXYDICARBONATE - RADICAL VERSUS NONRADICAL PATHWAY [J].
LEARDINI, R ;
NANNI, D ;
SANTORI, M ;
ZANARDI, G .
TETRAHEDRON, 1992, 48 (19) :3961-3970
[10]   AROMATIC ANNELATION BY REACTION OF ARYLIMIDOYL RADICALS WITH ALKYNES - EVIDENCE FOR THE INTERVENTION OF A SPIROCYCLOHEXADIENYL RADICAL IN THE SYNTHESIS OF SUBSTITUTED QUINOLINES [J].
LEARDINI, R ;
NANNI, D ;
PEDULLI, GF ;
TUNDO, A ;
ZANARDI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (09) :1591-1594