Synthesis and cycloaromatization kinetics of aromatic allene enynes

被引:27
作者
Dopico, PG [1 ]
Finn, MG [1 ]
机构
[1] Univ Virginia, Dept Chem, Charlottesville, VA 22901 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4020(98)01022-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aryl- and cyclopropyl-substituted allene enynes were prepared by a double olefination procedure from various aldehydes, and their cycloaromatization reactions were subjected to kinetics measurements in methanol and 1,4-cyclohexadiene solvents. The results support previous proposals of a polar diradical transition state for the cycloaromatization process. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:29 / 62
页数:34
相关论文
共 82 条
[1]  
AGIRBAS H, 1983, J CHEM SOC PERK T 2, P739
[2]   KINETICS OF REACTIONS OF CYCLOPROPYLCARBINYL RADICALS AND ALKOXYCARBONYL RADICALS CONTAINING STABILIZING SUBSTITUENTS - IMPLICATIONS FOR THEIR USE AS RADICAL CLOCKS [J].
BECKWITH, ALJ ;
BOWRY, VW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2710-2716
[3]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[4]   DOUBLE CYCLOAROMATIZATION OF (Z,Z)-DECA-3,7-DIENE-1,5,9-TRIYNE - EVIDENCE FOR THE INTERMEDIACY AND DIRADICAL CHARACTER OF 2,6-DIDEHYDRONAPHTHALENE [J].
BHARUCHA, KN ;
MARSH, RM ;
MINTO, RE ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3120-3121
[5]   CDPI3-ENEDIYNE AND CDPI3-EDTA CONJUGATES - A NEW CLASS OF DNA CLEAVING AGENTS [J].
BOGER, DL ;
ZHOU, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3018-3024
[6]   EVIDENCE OF REVERSIBLE RING-OPENING OF THE ALPHA-CYCLOPROPYLBENZYL RADICAL [J].
BOWRY, VW ;
LUSZTYK, J ;
INGOLD, KU .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (13) :923-925
[7]   SYNTHESIS AND OXIDATIVE ACTIVATION OF AN OXABICYCLO[7.2.1] ENEDIYNE [J].
BRANDSTETTER, T ;
MAIER, ME .
TETRAHEDRON, 1994, 50 (05) :1435-1448
[8]   INTERNAL HYDROGEN ABSTRACTION BY ACTIVATED NEOCARZINOSTATIN - QUENCHING OF THE RADICAL AT C2 BY HYDROGEN-ATOM TRANSFER FROM THE ALPHA-CARBON OF THE ADDUCTED THIOL [J].
CHIN, DH ;
GOLDBERG, IH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1914-1915
[9]   METHYLENECYCLOPROPANE REARRANGEMENT AS A PROBE FOR FREE-RADICAL SUBSTITUENT EFFECTS - SIGMA.-VALUES FOR COMMONLY ENCOUNTERED CONJUGATING AND ORGANOMETALLIC GROUPS [J].
CREARY, X ;
MEHRSHEIKHMOHAMMADI, ME ;
MCDONALD, S .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3254-3263
[10]   MODE OF REVERSIBLE BINDING OF NEOCARZINOSTATIN CHROMOPHORE TO DNA - EVIDENCE FOR BINDING VIA THE MINOR GROOVE [J].
DASGUPTA, D ;
GOLDBERG, IH .
BIOCHEMISTRY, 1985, 24 (24) :6913-6920