Abstract
The reaction of aryl substituted α,β-unsaturated nitroalkenes 1a-g with triallylaluminum 2 in ether solution at 0°C generated low to high yields of 4,5-unsaturated nitroalkenes 3a-g after adding the nitronate to an ice-cold solution of dilute hydrobromic acid. The yields of products 3h-j were increased substantially when the alkyl substituted α,β-unsaturated nitroalkene 1h and the highly hindered α,β-unsaturated nitroalkenes 1i and 1j reacted with 2 in the presence of aluminum chloride. The most important thing is triallylaluminum was prepared from allyl bromide and pure elemental Al, not from Grignard reagent.
Original language | English |
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Pages (from-to) | 3677-3687 |
Number of pages | 11 |
Journal | Synthetic Communications |
Volume | 37 |
Issue number | 20 |
DOIs | |
Publication status | Published - 2007 Jan |
Keywords
- 4,5-unsaturated nitroalkenes
- Conjugate addition
- Triallylaluminum
- α,β-unsaturated nitroalkenes
ASJC Scopus subject areas
- Organic Chemistry