74207-61-7Relevant academic research and scientific papers
Alkyne-enol ether cross-metathesis in the presence of CuSO4: Direct formation of 3-substituted crotonaldehydes in aqueous medium
Castagnolo, Daniele,Botta, Lorenzo,Botta, Maurizio
supporting information; experimental part, p. 3172 - 3174 (2009/08/07)
An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO4 and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from
PREFERENTIAL FORMATION OF THE Z ISOMERS OF CINNAMALDEHYDES IN THE REARRANGEMENT OF ARYLETHYNYLCARBINOLS CATALYZED BY POLYVANADIOORGANOSILOXANES
Gulyi, S. E.,Erman, M. B.,Novikov, N. A.,Aul'chenko, I. S.,Vol'pin, M. E.
, p. 715 - 721 (2007/10/02)
During the rearrangement of secondary and tertiary aryl(ethynyl)carbinols, catalyzed by polyvanadioorganosiloxanes, the thermodynamically less favorable Z isomers of the cinnamaldehydes are formed preferentially.It was shown that zero order in the initial carbinol and pseudofirst order in the catalyst are observed in the rearrangement.The activation parameters of the reaction, which confirm that the rearrangement takes place through a highly polar cyclic transition state, were determined.The dependence of the reaction rate on the structure of the initial carbinol is discussed.The Z-stereoselectivity of the rearrangement is explained by the presence of steric effects, which show up at the stage of the conversion of the intermediate allenyl vanadate into cinnamaldehyde.
SOME FEATURES OF THE REARRANGEMENT OF TERTIARY ETHYNYLCARBINOLS IN THE PRESENCE OF POLYVANADIOORGANOSILOXANES
Erman, M. B.,Aul'chenko, I. S.,Kheifits, L. A.
, p. 21 - 28 (2007/10/02)
The rearrangement of various tertiary ethynylcarbinols to α,β-unsaturated aldehydes, catalyzed by polyvanadioorganosiloxanes, was studied, and the activation parameters of the reaction were determined.The structures of the side products were established, and proposals were made about the mechanism of their formation.Additives which suppress the side reactions were found.As a result the yields of the unsaturated aldehydes were increased significantly.
