4.5 Review

Keteniminium Ions: Unique and Versatile Reactive Intermediates for Chemical Synthesis

Journal

SYNTHESIS-STUTTGART
Volume 49, Issue 15, Pages 3183-3214

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588452

Keywords

keteniminium ions; ketenimines; ynamines; ynamides; amides; reactive intermediates

Funding

  1. Universite libre de Bruxelles (ULB)
  2. FNRS [CDR J.0058.17 Keteniminium]
  3. Fonds pour la formation a la Recherche dans l'Industrie et dans l'Agriculture (F.R.I.A.)

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Keteniminium ions have been demonstrated to be remarkably useful and versatile reactive intermediates in chemical synthesis. These unique heterocumulenes are pivotal electrophilic species involved in a number of efficient and selective transformations. More recently, even more reactive 'activated' keteniminium ions bearing an additional electron-withdrawing group on the nitrogen atom have been extensively investigated. The chemistry of these unique reactive intermediates, including representative methods for their in situ generation, will be overviewed in this review article.

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