Cyclization of aryl acyl radicals generated from S-(4-cyano)phenyl thiolesters by a nickel complex catalyzed electroreduction

被引:36
作者
Ozaki, S [1 ]
Adachi, M [1 ]
Sekiya, S [1 ]
Kamikawa, R [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Osaka 5650871, Japan
关键词
D O I
10.1021/jo0268512
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic acyl radicals generated from S-(4-cyano)phenyl 2-alkenylthiobenzoate by a nickel complex catalyzed electroreduction undergo 5- and 6-exo cyclization to give 1-indanone and dihydro-1-naphthalenone derivatives, respectively.
引用
收藏
页码:4586 / 4589
页数:4
相关论文
共 23 条
[1]  
BACHI MD, 1989, HETEROCYCLES, V28, P583
[2]   ACYL RADICAL CYCLIZATIONS IN SYNTHESIS .5. FURTHER TANDEM PROCESSES - FORMATION OF AN ALPHA-METHYLENECYCLOHEXANONE BY A CYCLIZATION-FRAGMENTATION HYDROGEN-ABSTRACTION SEQUENCE [J].
BATTY, D ;
CRICH, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (23) :3205-3209
[3]   Generation and intermolecular reactions of 2-indolylacyl radicals [J].
Bennasar, ML ;
Roca, T ;
Griera, R ;
Bosch, J .
ORGANIC LETTERS, 2001, 3 (11) :1697-1700
[4]   ACYL RADICALS - INTERMOLECULAR AND INTRAMOLECULAR ALKENE ADDITION-REACTIONS [J].
BOGER, DL ;
MATHVINK, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1429-1443
[5]   INTRAMOLECULAR ACYL RADICAL ALKENE ADDITION-REACTIONS - MACROCYCLIZATION REACTIONS [J].
BOGER, DL ;
MATHVINK, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4008-4011
[6]   KINETIC AND SPECTROSCOPIC STUDIES ON ACYL RADICALS IN SOLUTION BY TIME-RESOLVED INFRARED-SPECTROSCOPY [J].
BROWN, CE ;
NEVILLE, AG ;
RAYNER, DM ;
INGOLD, KU ;
LUSZTYK, J .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (02) :363-379
[7]  
Chatgilialoglu C, 1997, CHEM-EUR J, V3, P376
[8]   PHOTOINDUCED FREE-RADICAL CHEMISTRY OF THE ACYL TELLURIDES - GENERATION, INTERMOLECULAR AND INTRAMOLECULAR TRAPPING, AND ESR SPECTROSCOPIC IDENTIFICATION OF ACYL RADICALS [J].
CRICH, D ;
CHEN, C ;
HWANG, JT ;
YUAN, HW ;
PAPADATOS, A ;
WALTER, RI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :8937-8951
[9]   Generation and cyclization of acyl radicals from thiol esters under nonreducing, tin-free conditions [J].
Crich, D ;
Hao, XL .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5982-5988
[10]   THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .2. [J].
CURRAN, DP .
SYNTHESIS-STUTTGART, 1988, (07) :489-513