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RESEARCH ARTICLE
Contents Vol 64(1)

Some Organometallic Chemistry of Tetracyanoethene: CN-displacement and Cycloaddition Reactions with Alkynyl–Transition Metal Complexes and Related Chemistry

Michael I. Bruce A
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Physics, University of Adelaide, SA 5005, Australia. Email: michael.bruce@adelaide.edu.au

Australian Journal of Chemistry 64(1) 77-103 https://doi.org/10.1071/CH10307
Submitted: 18 August 2010  Accepted: 29 October 2010   Published: 14 January 2011

Abstract

The highly electron-deficient cyanocarbons tetracyanoethene (tcne) and, to a lesser extent, tetracyanoquinodimethane (tcnq), display a fascinating chemistry with transition metal substrates. In particular, the [2 + 2]-cycloadditions of the cyanocarbons with alkynyl- or poly-ynyl–metal complexes have been extensively studied by the author’s group. These reactions proceed via polar adducts to give σ-cyclobutenyl complexes, which then undergo facile ring-opening (retro-electrocyclic) reactions to form the corresponding butadienyl derivatives. In some cases, further reactions can occur by displacement of weakly bound ligands from the metal centre. The subsequent chemistry of these derivatives has been only cursorily investigated, while related studies of organic analogues have produced molecules with interesting electronic and optical properties.


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