SYNTHESIS AND REACTIVITY OF THE FIRST BIS(CROWN ETHER) ENEDIYNE

被引:38
作者
KONIG, B
RUTTERS, H
机构
[1] Institut für Organische Chemie der Technischen Universität Braunschweig, D-38106 Braunschweig
关键词
D O I
10.1016/S0040-4039(00)73220-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a new bis(crown ether)-enediyne 3 via palladium catalyzed coupling reactions is described. On treatment with sodium-hexafluorophosphate two cations are bound by the title compound 3; with potassium ions the sandwich complex 5 is formed. The thermal reactivity of the enediyne moiety towards cyclisation was investigated by differential scanning calorimetry, whereby the metal complexes showed an increased stability.
引用
收藏
页码:3501 / 3504
页数:4
相关论文
共 33 条
[11]   COMPLEXES OF PLATINUM METALS WITH CROWN ETHERS CONTAINING TERTIARY PHOSPHINE-SUBSTITUTED BENZO GROUPS [J].
HYDE, EM ;
SHEPHERD, I ;
SHAW, BL .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1978, (12) :1696-1705
[12]   CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].
LEE, MD ;
DUNNE, TS ;
SIEGEL, MM ;
CHANG, CC ;
MORTON, GO ;
BORDERS, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466
[13]  
LINSTRUMELLE G, 1985, TETRAHEDRON LETT, V26, P3811
[14]   KINETIC EVIDENCE FOR THE FORMATION OF DISCRETE 1,4-DEHYDROBENZENE INTERMEDIATES - TRAPPING BY INTERMOLECULAR AND INTRAMOLECULAR HYDROGEN-ATOM TRANSFER AND OBSERVATION OF HIGH-TEMPERATURE CIDNP [J].
LOCKHART, TP ;
COMITA, PB ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4082-4090
[15]   EVIDENCE FOR THE REACTIVE SPIN STATE OF 1,4-DEHYDROBENZENES [J].
LOCKHART, TP ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4091-4096
[16]   OXIDATIVE GENERATION OF AN ENEDIYNE SYSTEM FROM A 1,5-DIYNE PRECURSOR - A NOVEL TRIGGERING DEVICE FOR ENEDIYNES [J].
MAIER, ME ;
BRANDSTETTER, T .
TETRAHEDRON LETTERS, 1991, 32 (30) :3679-3682
[17]   DESIGN AND SYNTHESIS OF A SYSTEM FOR ENEDIYNE FORMATION BY ANTHRAQUINONE REDUCTIVE ACTIVATION [J].
MYERS, AG ;
DRAGOVICH, PS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5859-5860
[18]   ENEDIYNE COMPOUNDS EQUIPPED WITH ACID-SENSITIVE, BASE-SENSITIVE AND PHOTO-SENSITIVE TRIGGERING DEVICES - CHEMICAL SIMULATION OF THE DYNEMICIN A REACTION CASCADE [J].
NICOLAOU, KC ;
DAI, WM ;
WENDEBORN, SV ;
SMITH, AL ;
TORISAWA, Y ;
MALIGRES, P ;
HWANG, CK .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (08) :1032-1036
[19]   A NEW CLASS OF DNA-CLEAVING MOLECULES - PH-DEPENDENT DNA CLEAVAGE BY PROPARGYLIC AND ALLENIC SULFONES [J].
NICOLAOU, KC ;
SKOKOTAS, G ;
MALIGRES, P ;
ZUCCARELLO, G ;
SCHWEIGER, EJ ;
TOSHIMA, K ;
WENDEBORN, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (09) :1272-1275
[20]  
NICOLAOU KC, 1993, ANGEW CHEM, V105, P1462