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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Carbocations

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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Phosphorus-stabilized titanium carbene complexes: synthesis, reactivity and DFT studies.

Mathieu Lafage1, Hadrien Heuclin, Xavier-Frédéric Le Goff

  • 1Laboratoire "Hétérochimie Fondamentale et Appliquée", Université Paul Sabatier, CNRS UMR 5069, 31062 Toulouse Cedex (France).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 24, 2014
PubMed
Summary

Novel titanium carbene complexes were synthesized from a bis(thiophosphinoyl)methanediide dianion. These complexes exhibit strong nucleophilic reactivity, leading to new diphosphinoketenimine compounds and providing insights into reaction mechanisms.

Keywords:
carbene ligandsdensity functional calculationsgeminal dianionsreaction mechanismstitanium

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Phosphorus Chemistry

Background:

  • Titanium carbene complexes are versatile synthetic intermediates.
  • Bis(thiophosphinoyl)methanediide (SCS^2-) is a unique geminal dianion ligand.
  • Understanding the reactivity of novel organometallic compounds is crucial for synthetic advancements.

Purpose of the Study:

  • To synthesize and characterize novel titanium carbene complexes.
  • To investigate the reactivity of these complexes with electrophiles.
  • To explore the formation of new phosphorus-containing organic compounds.

Main Methods:

  • Reaction of bis(thiophosphinoyl)methanediide dianion with titanium tetrachloride-bis(tetrahydrofuran).
  • X-ray crystallography for structural elucidation of titanium complexes and organic products.
  • Density Functional Theory (DFT) studies to rationalize reaction mechanisms.

Main Results:

  • Successful synthesis of bis-carbene complex [(SCS)2Ti] (2) and mono-carbene complex [(SCS)TiCl2(thf)] (3).
  • Demonstrated strong nucleophilic reactivity of the titanium carbene complexes towards ketones, aldehydes, N,N'-dicyclohexylcarbodiimide (DCC), and phenyl isocyanate.
  • Formation of novel diphosphinoketenimines (8a, 8b) and a bis-titanium guanidinate complex (9).

Conclusions:

  • The bis(thiophosphinoyl)methanediide ligand provides access to novel titanium carbene complexes.
  • These complexes display significant nucleophilic character, enabling the synthesis of diverse organophosphorus compounds.
  • DFT studies elucidated the reaction mechanism involving DCC, highlighting the utility of these titanium complexes in organic synthesis.