Synthesis of New Halo-Containing Enynes: Reaction of Lithium Acetylenides with 1,1,1-Trihalo-4-alkoxy-3-buten-2-ones

Title: Synthesis of New Halo-Containing Enynes: Reaction of Lithium Acetylenides with 1,1,1-Trihalo-4-alkoxy-3-buten-2-ones

Volume: 4 Issue: 3

Author(s): Marcos A. P. Martins, Marcelo Rossatto, Clarissa P. Frizzo, Pablo Machado, Lucas Pizzuti, Daniel Emmerich, Joao I. Pereira, Sergio Brondani, Nilo Zanatta, Helio G. Bonacorso and Alex F. C.Flores

Affiliation:

Keywords: Enynes, acetylenes, halo-ketones

Abstract: The reaction of lithium acetylenide ((R-C°CLi, where R = Ph, Pent, Bu) with 1,1,1-trihalo-4-alcoxy- 3-alken-2-ones [CX3C(O)C(R2)=C(R1)-OR3, where X = Cl, F; R1, R2 = H, Me; R3 = Me, Et] in the presence of BF3·Et2O to give 1,4- or 1,2-addition products is reported. The regiospecific formation of 1,4-addition products was observed for substrates with R1 = H, and for substrates which had the methyl group on C-4 (R1 = Me), the formation of 1,2-addition products was favored.

Cite this article as:

P. Martins A. Marcos, Rossatto Marcelo, Frizzo P. Clarissa, Machado Pablo, Pizzuti Lucas, Emmerich Daniel, Pereira I. Joao, Brondani Sergio, Zanatta Nilo, Bonacorso G. Helio and C.Flores F. Alex, Synthesis of New Halo-Containing Enynes: Reaction of Lithium Acetylenides with 1,1,1-Trihalo-4-alkoxy-3-buten-2-ones, Letters in Organic Chemistry 2007; 4 (3) . https://dx.doi.org/10.2174/157017807780737264