Synthesis, structural characterization, and coordination chemistry of imidazole-based alkylidene ketenes

被引：23

作者：

Feuerstein, Wolfram ^{[1
]}

Varava, Paul ^{[1
]}

Fadaei-Tirani, Farzaneh ^{[1
]}

Scopelliti, Rosario ^{[1
]}

Severin, Kay ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne EPFL, Inst Sci & Ingn Chim, CH-1015 Lausanne, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 87期

关键词：

FLASH-VACUUM PYROLYSIS; MICROWAVE-SPECTRUM; CARBODICARBENES; GENERATION; LIGAND; DIFLUOROVINYLIDENE; METHYLENEKETENES; PROPADIENONE; CUMULENONES; COMPLEXES;

D O I：

10.1039/d1cc05161j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Alkylidene ketenes typically display high intrinsic reactivity, impeding isolation on a preparative scale. Herein, we report the synthesis of alkylidene ketenes by reaction of imidazole-based diazoolefins with carbon monoxide. The good thermal stability of these heterocumulenes allows for characterization by single crystal X-ray diffraction. N-Heterocyclic alkylidene ketenes can be used as C-donor ligands for transition and main group metals, as evidenced by the isolation of complexes with AuCl, RhCl(CO)(2), PdCl(C3H5) and GaCl3.

引用

页码：11509 / 11512

页数：4

共 64 条

[1] STERIC AND INDENYL EFFECTS IN THE CHEMISTRY OF ALKYLIDYNE COMPLEXES OF TUNGSTEN AND MOLYBDENUM [J].

ANDERSON, S ;

HILL, AF ;

NASIR, BA .

ORGANOMETALLICS, 1995, 14 (06) :2987-2992

[2]

[Anonymous], Chem

[3] Isolation and reactivity of an elusive diazoalkene [J].

Antoni, P. W. ;

Golz, C. ;

Holstein, J. J. ;

Pantazis, D. A. ;

Hansmann, M. M. .

NATURE CHEMISTRY, 2021, 13 (06) :587-+

[4] N2/CO Exchange at a Vinylidene Carbon Center: Stable Alkylidene Ketenes and Alkylidene Thioketenes from 1,2,3-Triazole Derived Diazoalkenes [J].

Antoni, Patrick W. ;

Reitz, Justus ;

Hansmann, Max M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (32) :12878-12885

[5]

BENCHEIKH A, 1990, J CHEM SOC CHEM COMM, P615

[6]

Bent H., 1960, J CHEM ED, V37, P616, DOI DOI 10.1021/ED037P616

[7] AN APPRAISAL OF VALENCE-BOND STRUCTURES AND HYBRIDIZATION IN COMPOUNDS OF THE 1ST-ROW ELEMENTS [J].

BENT, HA .

CHEMICAL REVIEWS, 1961, 61 (03) :275-311

[8] The organometallic chemistry of Ph3P=C=C=O.: A route to metal-substituted ketenes [J].

Bertani, R ;

Casarin, M ;

Pandolfo, L .

COORDINATION CHEMISTRY REVIEWS, 2003, 236 (1-2) :15-33

[9] SIMPLE SYNTHESIS OF KETENYLIDENETRIPHENYLPHOSPHORANE AND ITS THIOANALOGS [J].

BESTMANN, HJ ;

SANDMEIER, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (09) :634-634

[10] Carboxy(vinyl)ketene intermediates in the thermolysis of methylthio- and methoxy-substituted Meldrum's acid derivatives [J].

Bibas, H ;

Kappe, CO ;

Wong, MW ;

Wentrup, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (03) :493-498

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