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

  • Pierre Vogel
  • Raymond Roulet

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.

Keywords

Adduct Ketone Hydride Octane Allyl 

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Copyright information

© Springer-Verlag Berlin Heidelberg 1989

Authors and Affiliations

  • Pierre Vogel
    • 1
  • Raymond Roulet
    • 1
  1. 1.Institut de chimie organique et Institut de chimie minérale et analytiqueUniversité de LausanneLausanneSwitzerland

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