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
[11]  
BUNUEL EE, 1985, ORGANOMETALLICS, V4, P1680
[12]  
Burth, 1995, ANGEW CHEM, V107, P881
[13]   FORMATION OF NITROXIDE RADICALS IN ALPHA-FERROCENYLCARBONIUM ION-NITROSOBENZENE SYSTEM [J].
CAIS, M ;
ASHKENAZI, P ;
DANI, S ;
GOTTLIEB, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 124 (01) :49-58
[14]  
CAIS M, 1964, J AM CHEM SOC, V86, P1148
[15]   MOLECULAR 2ND-ORDER OPTICAL NONLINEARITIES OF METALLOCENES [J].
CALABRESE, JC ;
CHENG, LT ;
GREEN, JC ;
MARDER, SR ;
TAM, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7227-7232
[16]   Reaction of sodium amalgam with carbenium ions species stabilised by two adjacent organometallic moieties [J].
Capon, JF ;
LeBerreCosquer, N ;
Kergoat, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 508 (1-2) :1-6
[17]   UNIMETAL SUPER BASES [J].
CAUBERE, P .
CHEMICAL REVIEWS, 1993, 93 (06) :2317-2334
[18]   A NEW FERROCENOPHANE SURFACE DERIVATIZING REAGENT FOR THE PREPARATION OF NEARLY REVERSIBLE ELECTRODES FOR HORSE HEART FERRICYTOCHROME-C FERROCYTOCHROME-C - 2,3,4,5-TETRAMETHYL-1-((DICHLOROSILYL)METHYL)[2]-FERROCENOPHANE [J].
CHAO, S ;
ROBBINS, JL ;
WRIGHTON, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (02) :181-188
[19]   IS N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE A GOOD LIGAND FOR LITHIUM [J].
COLLUM, DB .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (10) :448-454
[20]   FORMATION AND REACTIVITY OF HALOGEN-DERIVATIVES OF (ETA-5-CYCLOPENTADIENYL)THALLIUM [J].
CONWAY, BG ;
RAUSCH, MD .
ORGANOMETALLICS, 1985, 4 (04) :688-693