141023-06-5Relevant academic research and scientific papers
An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols
Aponick, Aaron,Li, Chuan-Ying,Malinge, Jeremy,Marques, Emerson Finco
supporting information; experimental part, p. 4624 - 4627 (2009/12/09)
Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargyllc alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles In minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.
A convenient and versatile method for the preparation of α-hydroxymethyl ketone derivatives from the corresponding allyl silyl ethers or allyl carboxylates
Hon, Yung-Son,Wong, Ying-Chieh,Wu, Kuo-Jui
experimental part, p. 896 - 914 (2009/12/06)
The ozonolysis of 1-substituted allyl silyl ethers or 1-substituted allyl carboxylates followed by treatment with bases gave the corresponding α-silyloxymethyl- or α-acyloxymethyl-ketones in good yields. It is proposed to proceed via the corresponding α-silyloxy- or α-acyloxyaldehydes intermediates followed by 1,4-group migration. The results of theoretical calculations are applicable to explain the experimental results.
