29138-80-5Relevant academic research and scientific papers
Substituted homoallenyl aldehydes and their derivatives. Part 1: Homoallenyl aldehydes and protected hydrazones
Galeta, Juraj,Man, Stanislav,Potacek, Milan
, p. 29 - 39 (2012/10/30)
The paper presents a simple synthesis of substituted propargyl vinyl ethers and their subsequent thermally-initiated Claisen rearrangement leading to various 3-substituted homoallenyl aldehydes. Several methods, including Sonogashira coupling, base-promoted substitution on the triple bond by sodium amide or butyllithium, and the preparation of substituted propargyl alcohols, were used in the initial step. Phosphate-protected homoallenyl aldehyde hydrazone derivatives were synthesised and fully characterised. The stereochemistry of 9-anthracene carbaldehyde hydrazone, which, surprisingly, afforded both cis and trans isomers, was established using X-ray analysis.
Cationic rhodium(I)-dppf complex-catalyzed olefin isomerization/propargyl claisen rearrangement/carbonyl migration cascade
Tanaka, Ken,Okazaki, Eri,Shibata, Yu
supporting information; experimental part, p. 10822 - 10823 (2009/12/03)
(Chemical Equation Presented) We have established that a cationic rhodium(I)-dppf complex catalyzes isomerizations of allyl propargyl ethers to allenic aldehydes in good yields from room temperature to 40°C. On the other hand, carbonyl migration reactions
Fused tetraeyclic heterocycles by thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylaldazines
Zachova, Hana,Man, Stanislav,Necas, Marek,Potacek, Milan
, p. 2548 - 2557 (2007/10/03)
The thermally initiated intramolecular criss-cross cycloaddition of 3-substituted homoallenylaldazines 5 has been explored. Their cyclization led to interesting new fused heterocyclic systems 6 consisting of four five-membered rings with two nitrogen hete
