The acid-promoted reaction of ethyl linoleate with nitrite. New insights from 15N-labelling and peculiar reactivity of a model skipped diene

Alessandra Napolitano, Orlando Crescenzi, Emanuela Camera, Italo Giudicianni, Mauro Picardo, Marco D'Ischia

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The acid-promoted reaction of ethyl linoleate with nitrite ions was re-examined by an integrated approach based on the use of 15NO2- combined with extensive GC-MS (EI, NICI, PICI) and 2D 1H,15N and 1H,13C NMR analysis. The less polar products proved to be regioisomeric E-nitroalkenes, novel Z-nitroalkenes, and 3-nitro-1,5-hexadienes derivatives. A medium polarity fraction consisted mainly of stereo- and regioisomeric 1,2-nitronitrates along with 1,5-dinitro-1,3-pentadiene compounds. Novel 5-nitro-2,4-pentadienone products could be identified in the most polar fraction, which featured 1,2-nitroalcohols as the most abundant components. Under similar conditions 1,4-hexadiene gave mainly a nitrofuroxan derivative.

Original languageEnglish
Pages (from-to)5061-5067
Number of pages7
JournalTetrahedron
Volume58
Issue number25
DOIs
Publication statusPublished - Jun 17 2002

Fingerprint

Nitrites
Labeling
Ions
Derivatives
Acids
Nuclear magnetic resonance
ethyl linoleate
1,3-pentadiene
1,5-hexadiene
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
1,4-hexadiene

Keywords

  • Labelling
  • Lipids
  • Nitration
  • Nitrous acid and derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The acid-promoted reaction of ethyl linoleate with nitrite. New insights from 15N-labelling and peculiar reactivity of a model skipped diene. / Napolitano, Alessandra; Crescenzi, Orlando; Camera, Emanuela; Giudicianni, Italo; Picardo, Mauro; D'Ischia, Marco.

In: Tetrahedron, Vol. 58, No. 25, 17.06.2002, p. 5061-5067.

Research output: Contribution to journalArticle

Napolitano, Alessandra ; Crescenzi, Orlando ; Camera, Emanuela ; Giudicianni, Italo ; Picardo, Mauro ; D'Ischia, Marco. / The acid-promoted reaction of ethyl linoleate with nitrite. New insights from 15N-labelling and peculiar reactivity of a model skipped diene. In: Tetrahedron. 2002 ; Vol. 58, No. 25. pp. 5061-5067.
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