Conjugate addition of triallylaluminum to α,β-unsaturated nitroalkenes to produce 4,5-unsaturated nitroalkenes

Kao Hsien Shen, Ju Tsung Liu, Yih Ru Wu, Ching-Fa Yao

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 languageEnglish
Pages (from-to)3677-3687
Number of pages11
JournalSynthetic Communications
Volume37
Issue number20
DOIs
Publication statusPublished - 2007 Jan 1

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Hydrobromic Acid
Ice
Ether
allyl bromide
aluminum chloride

Keywords

  • 4,5-unsaturated nitroalkenes
  • Conjugate addition
  • Triallylaluminum
  • α,β-unsaturated nitroalkenes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Conjugate addition of triallylaluminum to α,β-unsaturated nitroalkenes to produce 4,5-unsaturated nitroalkenes. / Shen, Kao Hsien; Liu, Ju Tsung; Wu, Yih Ru; Yao, Ching-Fa.

In: Synthetic Communications, Vol. 37, No. 20, 01.01.2007, p. 3677-3687.

Research output: Contribution to journalArticle

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AU - Yao, Ching-Fa

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N2 - 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.

AB - 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.

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