Isolation of electronic from geometric contributions to Bergman cyclization of metalloenediynes

被引:23
作者
Bhattacharyya, S [1 ]
Clark, AE [1 ]
Pink, M [1 ]
Zaleski, JM [1 ]
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
关键词
D O I
10.1039/b301690k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Conformationally constrained ethylene-diamine metalloenediyne compounds exhibit alkyne termini separations that are constant and independent of metal center geometry. Ancillary chloride ligand electron donation into the Bergman cyclization reaction coordinate, however, dramatically influences the observed temperatures.
引用
收藏
页码:1156 / 1157
页数:2
相关论文
共 16 条
[1]   Metalloenediynes: Ligand field control of thermal Bergman cyclization reactions [J].
Benites, PJ ;
Rawat, DS ;
Zaleski, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7208-7217
[2]   REACTIVE 1,4-DEHYDROAROMATICS [J].
BERGMAN, RG .
ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (01) :25-31
[3]   Structure and thermal reactivity of a novel Pd(0) metalloenediyne [J].
Coalter, NL ;
Concolino, TE ;
Streib, WE ;
Hughes, CG ;
Rheingold, AL ;
Zaleski, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) :3112-3117
[4]   Electronic control of the Bergman cyclization: The remarkable role of vinyl substitution [J].
Jones, GB ;
Warner, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) :2134-2145
[5]  
KRAFT BJ, INORG CHEM, V42, P1663
[6]   DESIGN, SYNTHESIS, AND STUDY OF SIMPLE MONOCYCLIC CONJUGATED ENEDIYNES - THE 10-MEMBERED RING ENEDIYNE MOIETY OF THE ENEDIYNE ANTICANCER ANTIBIOTICS [J].
NICOLAOU, KC ;
ZUCCARELLO, G ;
RIEMER, C ;
ESTEVEZ, VA ;
DAI, WM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7360-7371
[7]   Ruthenium-mediated cycloaromatization of acyclic enediynes and dienynes at ambient temperature [J].
O'Connor, JM ;
Friese, SJ ;
Tichenor, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3506-3507
[8]   Inhibition and acceleration of the Bergman cycloaromatization reaction by the pentamethylcyclopentadienyl ruthenium cation [J].
O'Connor, JM ;
Lee, LI ;
Gantzel, P ;
Rheingold, AL ;
Lam, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (48) :12057-12058
[9]   Halo-enediynes: Probing the electronic and stereoelectronic contributions to the Bergman cycloaromatization [J].
Plourde, GW ;
Warner, PM ;
Parrish, DA ;
Jones, GB .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5369-5374
[10]   Substituent effects on the Bergman cyclization of (Z)-1,5-hexadiyne-3-enes: A systematic computational study [J].
Prall, M ;
Wittkopp, A ;
Fokin, AA ;
Schreiner, PR .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2001, 22 (13) :1605-1614