The acid-promoted reaction of ethyl linoleate with nitrite ions was re-examined by an integrated approach based on the use of (NO2-)-N-15 combined with extensive GC-MS (El, NICI, PICI) and 2D H-1, N-15 and H-1, C-13 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.
The acid-promoted reaction of ethyl linoleate with nitrite. New insights from 15N-labelling and peculiar reactivity of a model skipped diene
CRESCENZI, ORLANDO;D'ISCHIA, MARCO
2002
Abstract
The acid-promoted reaction of ethyl linoleate with nitrite ions was re-examined by an integrated approach based on the use of (NO2-)-N-15 combined with extensive GC-MS (El, NICI, PICI) and 2D H-1, N-15 and H-1, C-13 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
