371256-69-8Relevant academic research and scientific papers
One-pot consecutive reactions based on the synthesis of conjugated enones by the re-catalysed meyer-schuster rearrangement
Mattia, Elio,Porta, Alessio,Merlini, Valentina,Zanoni, Giuseppe,Vidari, Giovanni
supporting information, p. 11894 - 11898 (2012/10/29)
Re catalysis in one-pot reactions: An atom-economical, one-pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)-catalysed Meyer-Schuster rearrangement of the alkynol to provide α,β- unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels-Alder reaction of the enones provided products in good-to-high overall yields. Copyright
Zinc-mediated alkynylation of carbonyl compounds with iodoalkynes: a facile synthesis of propargyl alcohols
Srihari,Singh, Vinay K.,Bhunia, Dinesh C.,Yadav
scheme or table, p. 7132 - 7134 (2009/04/10)
A straightforward synthesis of propargyl alcohols from alkynyl iodides and carbonyl compounds using zinc is described.
Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins
Labrosse,Lhoste,Sinou
, p. 6634 - 6642 (2007/10/03)
Palladium-catalyzed condensation of benzene-1,2-diol with various propargylic carbonates, afforded regio- and stereoselectively 2,3-dihydro-2-ylidene-1,4-benzodioxins. The reaction is suggested to proceed by the formation of a (σ-allenyl)palladium complex, followed by the intermolecular attack of the phenoxide ion on this complex to generate a new (σ-allyl)palladium complex in equilibrium with the corresponding (η3-allyl)palladium complex. Intramolecular attack of the phenoxide ion afforded the corresponding benzodioxan compound. This last attack occurs predominantly at the more electrophilic end of the (η3-allyl)palladium intermediate. The Z- or E-stereochemistry of the products was established by 1H NMR and proton NOE measurements and also by X-ray analysis on an example. The Z-stereochemistry generally observed is in agreement with the formation of this (η3-allyl)palladium intermediate. However, in the case of tertiary propargylic carbonates, the E-stereochemistry generally observed could be explained by an intramolecular attack of the phenoxide ion on the intermediate (σ-allyl)palladium complex, in slow equilibrium with the (η3allyl)palladium complex.
