Russian Chemical Bulletin

, Volume 47, Issue 5, pp 913–917 | Cite as

Ruthenium- and palladium-catalyzed synthesis of polyfunctional 1,3-dienes

  • B. Seiller-Delevoye
  • C. Bruneau
  • P. H. Dixneuf
Organic Chemistry
  • 30 Downloads

Abstract

The ruthenium-catalyzed Markovnikov addition of acetic or benzoic acid to the triple bond of (E)-3-methylpent-2-en-4-yn-1-ol followed by acylation of the alcohol group in the diene formed under the action of low-toxic derivatives of carbonic and formic acids opens up a simple route to dienylic carbonates and formates. Activation of these esters by catalytic amounts of palladium(0) complexes under conditions of nucleophilic allylic substitution or decarboxylation affords functional dienes.

Key words

(E)-3-methylpent-2-en-4-yn-1-ol carboxylic acids, addition ruthenium(ii) complexes (E)-4-acetoxy(or benzyloxy)-3-methylpenta-2,4-dienyl-(2-methyl-3-oxobut-2-yl) carbonate, reaction with C- and O-nucleophiles (E)-3-methyl-5-formoxypenta-1,3-dien-2-yl benzoate decarboxylation tetrakis(triphenylphosphine)palladium 

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Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • B. Seiller-Delevoye
    • 1
  • C. Bruneau
    • 1
  • P. H. Dixneuf
    • 1
  1. 1.Laboratory of Coordination Chemistry and CatalysisNational Center of Scientific Research-University of RennesRennesFrance

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