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Org Lett. 2017 Apr 07;19(7):1882-1885. doi: 10.1021/acs.orglett.7b00648. Epub 2017 Mar 30.

Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide.

Organic letters

I Essid, C Laborde, F Legros, N Sevrain, S Touil, M Rolland, T Ayad, J-N Volle, J-L Pirat, D Virieux

Affiliations

  1. Institut Charles Gerhardt, CNRS UMR 5253, Ecole Nationale Supérieure de Chimie de Montpellier , 8 Rue de l'Ecole Normale, 34 296 Montpellier, France.
  2. Laboratoire de Chimie Organique des Hétéroéléments, Université de Carthage, Faculté des Sciences de Bizerte , 7021 Jarzouna, Tunisie.
  3. Institut Européen des Membranes - CC047, Université de Montpellier , 34095 Montpellier, France.
  4. PSL Research University, Chimie ParisTech-CNRS , Institut de Recherche de Chimie Paris, 11 Rue Pierre et Marie Curie, 75 005 Paris, France.

PMID: 28357865 DOI: 10.1021/acs.orglett.7b00648

Abstract

Bisphosphorylallenes were easily obtained in multigram scale from the Wittig-type rearrangement of bispropargyl alcohols. Unlike other conjugated bis-allenes, these reagents underwent a double cyclization mediated by iodine or copper dibromide leading to the formation of bis-1,2-oxaphospholenes.

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