Functionalized pentamethylferrocenes: Synthesis, structure, and electrochemistry

被引:55
作者
Bildstein, B [1 ]
Hradsky, A [1 ]
Kopacka, H [1 ]
Malleier, R [1 ]
Ongania, KH [1 ]
机构
[1] UNIV INNSBRUCK, INST ORGAN CHEM, A-6020 INNSBRUCK, AUSTRIA
基金
奥地利科学基金会;
关键词
iron; ferrocene; pentamethylferrocene; X-ray structure; electrochemistry;
D O I
10.1016/S0022-328X(97)00133-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The advantageous properties of the Cp* ligand - intensified electron donation, steric bulk, and enhanced solubility in comparison to the ubiquitous Cp ligand - are finding increasing use in organometallic chemistry. A systematic evaluation of synthetic routes to pentamethylferrocene compounds with a wide range of functionalities, including carboxyl, carbonyl, aminomethyl, vinyl, ethynyl, fulvenyl, cyclopentadienylmethyl, and others is reported, Spectroscopic, structural, and electrochemical properties of such functionalized pentamethylferrocenes Fc(*/2)-R compared to those of non-methylated ferrocenes Fc-R. The electronic influence of the Cp* ligand in these unsymmetrical ferrocenes Fc(*/2)-R has been studied by cyclic voltammetry measurements, demonstrating a decrease in oxidation potential of -0.276 V in direct comparison to non-methylated ferrocenes Fc-R. (C) 1997 Elsevier Science S.A.
引用
收藏
页码:127 / 145
页数:19
相关论文
共 98 条
[1]   A NEW STEROSELECTIVE APPROACH TO CHIRAL FERROCENYL LIGANDS FOR ASYMMETRIC CATALYSIS [J].
ABBENHUIS, HCL ;
BURCKHARDT, U ;
GRAMLICH, V ;
TOGNI, A ;
ALBINATI, A ;
MULLER, B .
ORGANOMETALLICS, 1994, 13 (11) :4481-4493
[2]   CONTRIBUTION TO STUDY OF METALLOCENES .24. MECHANISM OF LIGAND-EXCHANGE AND COMPLEXATION BY ALUMINUM-CHLORIDE OF FERROCENE AND ITS ALKYLATED AND ACYLATED DERIVATIVES [J].
ASTRUC, D ;
DABARD, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 111 (03) :339-347
[3]   AN IMPROVED SYNTHESIS OF FERROCENE-1,1'-DICARBALDEHYDE [J].
BALAVOINE, GGA ;
DOISNEAU, G ;
FILLEBEENKHAN, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 412 (03) :381-382
[4]   SYNTHESIS AND CHARACTERIZATION OF TRIMETALLOCENES AND TRIMETALLOCENIUM SALTS [J].
BARLOW, S ;
MURPHY, VJ ;
EVANS, JSO ;
OHARE, D .
ORGANOMETALLICS, 1995, 14 (07) :3461-3474
[5]   REDOX-RESPONSIVE SURFACTANTS - SYNTHESIS OF 1,1-DIFERROCENYL-N-ALKANES (C-1, C-5, C-7, C-19) VIA REACTION OF (DIFERROCENYL) METHYL CARBOCATION WITH CARBANIONS [J].
BILDSTEIN, B ;
DENIFL, P ;
WURST, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 496 (02) :175-186
[6]   TETRAFERROCENYLETHYLENE, A CHIRAL, ORGANOMETALLIC PROPELLER - SYNTHESIS, STRUCTURE, AND ELECTROCHEMISTRY [J].
BILDSTEIN, B ;
DENIFL, P ;
WURST, K ;
ANDRE, M ;
BAUMGARTEN, M ;
FRIEDRICH, J ;
ELLMERERMULLER, E .
ORGANOMETALLICS, 1995, 14 (09) :4334-4342
[7]  
BRANDSMA L, 1987, PREPARATIVE POLAR OR, V1, P38
[8]   PENTAMETHYLPENTALITHIORUTHENOCENE AND DECALITHIORUTHENOCENE [J].
BRETSCHNEIDERHURLEY, A ;
WINTER, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6468-6469
[9]   SYNTHESIS OF POLYENES THAT CONTAIN METALLOCENES VIA THE LIVING POLYMERIZATION OF ETHYNYLFERROCENE AND ETHYNYLRUTHENOCENE [J].
BUCHMEISER, M ;
SCHROCK, RR .
MACROMOLECULES, 1995, 28 (19) :6642-6649
[10]  
BUCHMEISER M, 1995, UNPUB