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

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, Alex F. C.Flores.

Journal Name: Letters in Organic Chemistry

Volume 4 , Issue 3 , 2007

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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.

Keywords: Enynes, acetylenes, halo-ketones

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Article Details

VOLUME: 4
ISSUE: 3
Year: 2007
Page: [193 - 197]
Pages: 5
DOI: 10.2174/157017807780737264
Price: $58

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