Thiophenol promoted radical cyclisation of hydrazones and oxime ethers

被引:19
作者
El Kaim, L [1 ]
Gacon, A [1 ]
Perroux, A [1 ]
机构
[1] Ecole Natl Super Tech Avancees, Lab Reacteurs & Proc, F-75015 Paris, France
关键词
D O I
10.1016/S0040-4039(97)10592-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Thiophenol radical induced cyclisation of N-dimethyltriazolyl imines is reported. Ethylenic but also acetylenic tethered hydrazones are cyclised to cycloalkyl hydrazine under smooth conditions. A comparative study with oxime ethers is described. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:371 / 374
页数:4
相关论文
共 15 条
[1]   THIOL-MEDIATED FREE-RADICAL CYCLIZATION OF ALKENYL AND ALKYNYL ISOCYANIDES [J].
BACHI, MD ;
BALANOV, A ;
BARNER, N .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7752-7758
[2]  
BOWMAN WR, 1995, TETRAHEDRON, V51, P7959
[3]   THIOPHENOL PROMOTED CYCLIZATION OF ENYNES [J].
BROKA, CA ;
REICHERT, DEC .
TETRAHEDRON LETTERS, 1987, 28 (14) :1503-1506
[4]  
ELKAIM L, 1996, TETRAHEDRON LETT, V61, P1556
[5]  
Giese B., 2004, Organic Reactions, P301, DOI [10.1002/0471264180.or048.02, DOI 10.1002/0471264180.OR048.02]
[6]   A NOVEL AND CONCISE SYNTHESIS OF AMINOCYCLOPENTITOLS AND 1-DEOXYNOJIRIMYCIN VIA RADICAL CYCLIZATION OF OXIME ETHERS [J].
KIGUCHI, T ;
TAJIRI, K ;
NINOMIYA, I ;
NAITO, T ;
HIRAMATSU, H .
TETRAHEDRON LETTERS, 1995, 36 (02) :253-256
[7]   NOVEL RADICAL CYCLIZATION OF N-AZIRIDINYL IMINES [J].
KIM, S ;
KEE, IS ;
LEE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9882-9883
[8]   FURTHER-STUDIES ON RADICAL CYCLIZATIONS OF N-AZIRIDINYL IMINES - CARBONYL AND ALKENYL GROUP VS N-AZIRIDINYL IMINO GROUP COMPETITION [J].
KIM, S ;
KEE, IS .
TETRAHEDRON LETTERS, 1993, 34 (26) :4213-4214
[9]   THIYL RADICAL INDUCED CYCLIZATIONS OF DIENES - CYCLIZATION OF ALPHA-ACORADIENE, ALPHA-BULNESENE, AND GERANYL ACETATE TO CEDRANE, PATCHULANE, AND CYCLOGERANYL ACETATE PRODUCTS [J].
KUEHNE, ME ;
DAMON, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) :1825-1832
[10]   THIYL RADICAL AND MERCURIC ION INDUCED CYCLIZATIONS OF DIMETHYL DIPROPARGYLMALONATE AND DIMETHYL PROPARGYL-3-THIYLALLYLMALONATES [J].
KUEHNE, ME ;
PARSONS, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (21) :3408-3410