Synthesis, Table of Contents

Synthesis 2017; 49(23): 5131-5142
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. Bencke

^aLaboratory of Chemistry, Instituto Federal Catarinense, 89240-000, São Francisco do Sul, SC, Brazil

,

Mário A. Marangoni

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

,

Adriano F. Camargo

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

,

Cassio A. Fantinel

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

,

Helio G. Bonacorso

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

,

Marcos A. P. Martins

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

,

Nilo Zanatta *

^bNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil Email: nilo.zanatta@ufsm.br

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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.

Key words

Key words

pentadienenitriles - olefination - enones - diethyl cyanomethylphosphonate - Horner–Wadsworth–Emmons reaction

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Supplementary Material

Supplementary Material

Supporting Information