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Synthesis and Structure of Carbonyliron Complexes of Allenecarboxylates and Allenic Lactones


Trifonov, Latchezar S; Orahovats, Alexander S; Prewo, Roland; Heimgartner, Heinz (1988). Synthesis and Structure of Carbonyliron Complexes of Allenecarboxylates and Allenic Lactones. Helvetica Chimica Acta, 71(3):551-561.

Abstract

On irradiation in the presence of Fe(CO)5, the allenecarboxylates 1 afforded binuclear carbonyliron complexes 6 (Scheme 3), whereas the allenic lactone 7 under similar conditions gave a mixture of one binuclear and two mononuclear carbonyliron complexes (9, 8, and 10; Scheme 4). The structure of the complexes has been elucidated by X-ray crystallography. The structure of the binuclear complex 9 corresponds to that of 6, while 8 has been shown to be a 1,3-butadiene(tricarbonyl)iron complex. The unique structure of 10 represents a new type of allenic complex. A stepwise formation of the complexes via intermediate allene(tetracarbony1)iron complexes of type 11 and 13 is suggested. Treatment of the binuclear complex 6h with FeCI3 led to the formation of the free ligand and a mixture of mononuclear complexes 13 and 14 (Scheme 5). On heating, the 1,3-diene complex 8 yielded the free ligand 15, the product of a (1,3) H shift in the allene 7; the complex 10 on the other hand liberates 7 on treatment with ethylenetetracarbonitrile (TCNE) (Scheme 6).

Abstract

On irradiation in the presence of Fe(CO)5, the allenecarboxylates 1 afforded binuclear carbonyliron complexes 6 (Scheme 3), whereas the allenic lactone 7 under similar conditions gave a mixture of one binuclear and two mononuclear carbonyliron complexes (9, 8, and 10; Scheme 4). The structure of the complexes has been elucidated by X-ray crystallography. The structure of the binuclear complex 9 corresponds to that of 6, while 8 has been shown to be a 1,3-butadiene(tricarbonyl)iron complex. The unique structure of 10 represents a new type of allenic complex. A stepwise formation of the complexes via intermediate allene(tetracarbony1)iron complexes of type 11 and 13 is suggested. Treatment of the binuclear complex 6h with FeCI3 led to the formation of the free ligand and a mixture of mononuclear complexes 13 and 14 (Scheme 5). On heating, the 1,3-diene complex 8 yielded the free ligand 15, the product of a (1,3) H shift in the allene 7; the complex 10 on the other hand liberates 7 on treatment with ethylenetetracarbonitrile (TCNE) (Scheme 6).

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1988
Deposited On:14 May 2014 09:12
Last Modified:21 Nov 2017 17:20
Publisher:Wiley-Blackwell
ISSN:0018-019X
Funders:F. Hoffmann-La Roche & Co. AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.19880710307

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