Unexpected C-C Bond Formation with a Ferrocenyl Fischer Carbene Complex

被引：1

作者：

Veit, Philipp ^{[1
]}

Seibert, Sebastian ^{[1
]}

Foerster, Christoph ^{[1
]}

Heinze, Katja ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE | 2020年 / 646卷 / 13期

关键词：

Carbene complexes; Chromium; C-C coupling; Cyclobutenone; Ferrocene; DOTZ REACTION; BASIS-SETS; CHEMICAL MULTITALENTS; NUCLEOPHILE ADDITION; CHROMIUM; ALKYNES; CYCLOBUTENONES; INSERTION; TUNGSTEN; LIGANDS;

D O I：

10.1002/zaac.201900350

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Thermolysis of (OC)(5)Cr(C(OEt)(Fc)) (1) gives 2,N-diferrocenyl acetamide Fc-CH2-CO-NH-Fc (2) in the presence of amino ferrocene Fc-NH2. In the absence of a nucleophile, 4-ethoxy-2,3,4-triferrocenyl-cyclobut-2-enone (3) forms from 1 under thermal activation. Single crystal X-ray diffraction, NMR spectroscopy and mass spectrometry unambiguously confirm the structure of both unexpected products. Quantum chemical calculations and kinetic experiments by mass spectrometry and IR spectroscopy help to propose conceivable pathways to their formation.

引用

页码：940 / 947

页数：8

共 50 条

[1] Unexpected C-C bond cleavage and C-C bond formation observed in the reaction of a cationic iridium complex with heteroatom-substituted cyclopropanes
Anstey, Mitchell R.
Yung, Cathleen M.
Du, Juana
Bergman, Robert G.
Journal of the American Chemical Society, 2007, 129 (04): : 776 - 777
[2] Unexpected C-C bond cleavage and C-C bond formation observed in the reaction of a cationic iridium complex with heteroatom-substituted cyclopropanes
Anstey, Mitchell R.
Yung, Cathleen M.
Du, Juana
Bergman, Robert G.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) : 776 - 777
[3] Redox Noninnocence of Carbene Ligands: Carbene Radicals in (Catalytic) C-C Bond Formation
Dzik, Wojciech I.
Zhang, X. Peter
de Bruin, Bas
INORGANIC CHEMISTRY, 2011, 50 (20) : 9896 - 9903
[4] Catalytic functionalization of methane by carbene insertion and C-C bond formation
Perez, Pedro J.
Caballero, Ana
Mar Diaz-Requejo, M.
Olmos, Andrea
Angeles Fuentes, M.
Etienne, Michel
Despagne-Ayoub, Emmanuelle
Ojo, Wilfried-Solo
Munoz, Bianca K.
Asensio, Gregorio
Elena Gonzalez-Nunez, M.
Mello, Rosella
Diaz-Rodriguez, Alba
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[5] INOR 303-Unexpected C-C bond cleavage and C-C bond formation observed in the reaction of a cationic iridium complex with heteroatom-substituted cyclopropanes
Anstey, Mitchell R.
Yung, Cathleen M.
Du, Juana
Bergman, Robert G.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[6] C-Cα insertion:: Insertion of an alkyne into the C-C single bond between the carbene-carbon atom and the α-carbon atom of a Fischer carbene complex by an unprecedented metalla(di-π-methane) skeletal rearrangement
Ünaldi, S
Aumann, R
Fröhlich, R
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) : 3300 - 3309
[7] Unexpected Formation of a Cyclopentadienylruthenium Alkoxycarbonyl Complex with a Coordinated C=C Bond
Aberg, Jenny B.
Warner, Madeleine C.
Backvall, Jan-E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13622 - +
[8] REACTION OF METAL CARBENE COMPLEXES WITH CYCLOBUTENEDIONES - THE 1ST GENERAL C-C BOND INSERTION REACTION FOR FISCHER CARBENE COMPLEXES
ZORA, M
HERNDON, JW
ORGANOMETALLICS, 1993, 12 (02) : 248 - 249
[9] Unexpected formation of a cyclopentadienylruthenium alkoxycarbonyl complex with a coordinated C=C bond
Aberg, Jenny B.
Warner, Madeleine C.
Backvall, Jan E.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 239
[10] Photocatalysis for the formation of the C-C bond
Fagnoni, Maurizio
Dondi, Daniele
Ravelli, Davide
Albini, Angelo
CHEMICAL REVIEWS, 2007, 107 (06) : 2725 - 2756

← 1 2 3 4 5 →