Synthesis
DOI: 10.1055/s-0036-1590871
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Penta-2,4-dienenitriles by the Horner–Wadsworth–Emmons Olefination of Enones

Carlos E. Benckea, Mário A. Marangonib, Adriano F. Camargob, Cassio A. Fantinelb, Helio G. Bonacorsob, Marcos A. P. Martinsb, Nilo Zanatta*b
  • aLaboratory of Chemistry, Instituto Federal Catarinense, 89240-000, São Francisco do Sul, SC, Brazil
  • bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Email: nilo.zanatta@ufsm.br
The authors are grateful for financial support from the Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS/CNPq – PRONEX – Grant No. 16/2551-0000477-3) and fellowships from CNPq (C.E.B., C.A.F.), CAPES (M.A.M.), and FAPERGS (A.F.C.).
Further Information

Publication History

Received: 14 June 2017

Accepted after revision: 18 July 2017

Publication Date:
24 August 2017 (eFirst)

Abstract

Three new series of compounds, 5-alkoxy-3-(trifluoromethyl)penta-2,4-dienenitriles, 5-(phenylthio)-3-(trifluoromethyl)penta-2,4-dienenitriles, and ethyl 4-alkoxy-2-(cyanomethylene)but-3-enoates, obtained from the olefination reaction of the respective enones with diethyl cyanomethylphosphonate via the Horner–Wadsworth–Emmons olefination are reported. All products were obtained as single regioisomers; however, the composition of the stereoisomers changed according to the enone substituents. A study based on 1H and 13C NMR chemical shifts, 1H–19F and 13C–19F NMR coupling constants, 1H NMR signal integrals, and HSQC, HMBC, and NOESY experiments was performed in order to assign the structure and percentage of each stereoisomer obtained.

Supporting Information