Highly stereoselective synthesis of functionalized 1,3-dienes from a new allyl bromide

Authors

  • Asma Fray Department of Chemistry, University of Tunis El Manar, Faculty of Science, Campus, 2092 Tunis, Tunisia
  • Jihene Ben Kraiem Laboratoire Méthodes et Techniques d'Analyse (LMTA), Institut National de Recherche et d'Analyse Physico-chimique (INRAP) Biotechnôpole Sidi-Thabet, 2020 Tunis, Tunisia.
  • Hassen Amri Department of Chemistry, University of Tunis El Manar, Faculty of Science, Campus, 2092 Tunis, Tunisia

DOI:

https://doi.org/10.13171/mjc.3.3.2014.12.06.01

Abstract

New and highly functionalized 1,3-dienes 3 and 4 have been synthesized via two different pathways starting from allyl bromide 1. Firstly, the reaction of allyl bromide 1 with triethylphosphite leads to an allylphosphonate 2, which undergoes the Wittig-Horner reaction with a range of saturated and unsaturated aldehydes gives rise to the corresponding 1,3-dienes 3. Secondly, a highly stereoselective reaction between allyl bromide 1 and nitroalkane salts, offers the possibility to obtaining functionalized (E)-1,3-dienes 4.

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Published

2014-06-12

Issue

Vol. 3 No. 3 (2014)

Section

Organic Chemistry

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