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Ironcarbonyl Complexes of Exocyclic Polyenes. The Tricarbonyl(1,3-Diene)Iron Moiety as Remote Substituent

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Organometallics in Organic Synthesis 2

Abstract

The mono and dimetallic ironcarbonyl complexes of 5,6,7,8-tetramethylidenebicyclo[2.2.2]oct-2-ene, 5,6,7,8-tetramethylidenebicyclo[2.2.2]oct-2-yl and of 3,4,6,7-tetramethylidenebicyclo[2.2.1]oct-2-yl derivatives can be prepared stereoselectively. Their chemistry has been investigated and has unveiled several cases of useful lateral control by remote (diene)Fe(CO)3 moieties in SN1 solvolyses of esters, Friedel-Crafts acylation of (diene)Fe(CO)3 systems, nucleophilic reductions of ketones, hydrogen/deuterium exchanges of methylene groups α to carbonyl functions, and in Diels-Alder additions of exocyclic s-cis-butadiene moieties grafted onto bicyclic skeletons. The remote (diene)Fe(CO)3 group influences on the reactions through steric effects due to its bulk or/and through electronic effects. Depending on the electron demand of the reaction, the remote (diene)Fe(CO)3 group can act either as an electron-withdrawing substituent (inductive effect due to its permanent dipole) or as an electron-releasing substituent due to its polarisability.

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  1. Institut de chimie organique et Institut de chimie minérale et analytique, Université de Lausanne, CH-1005, Lausanne, Switzerland

    Pierre Vogel & Raymond Roulet

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  1. Pierre Vogel
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  1. Institut für Anorganische Chemie der Universität Würzburg, Am Hubland, D-8700, Würzburg, Germany

    Helmut Werner

  2. Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-8700, Würzburg, Germany

    Gerhard Erker

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Vogel, P., Roulet, R. (1989). Ironcarbonyl Complexes of Exocyclic Polyenes. The Tricarbonyl(1,3-Diene)Iron Moiety as Remote Substituent. In: Werner, H., Erker, G. (eds) Organometallics in Organic Synthesis 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-74269-9_5

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