1007129-33-0Relevant academic research and scientific papers
Palladium-catalyzed reactions of 3-substituted methylenecyclopropanes
Shao, Li-Xiong,Li, Jia,Wang, Bao-Yu,Shi, Min
supporting information; experimental part, p. 6448 - 6453 (2011/02/21)
Pd-catalyzed reactions of 3-substituted methylenecyclopropanes (MCPs), in which the substituents can be either hydroxymethyl or formyl, have been thoroughly investigated in the presence or absence of an acid source. It was found that the Pd-catalyzed reactions of methylenecyclopropylcarbinols (Z)-1 in the presence of acetic acid, acetic acid 2-methylene-but-3-enyl esters 4 can be formed in moderate yields. It was also found that Pd alone can catalyze the isomerization of methylenecyclopropylcarbinols (E)-1 in the absence of an acid source to form pent-4-enals 3. The Pd-catalyzed reactions of methylenecyclopropanecarbaldehydes 5 were also carried out in the presence of acetic acid. It was found that when (E)-5 was used as the substrate, the isomerized product, penta-2,4-dienal 6, could be obtained in good to high yields, whereas the use of (Z)-5 gave 2-(3-formylpenta-2,4-dienylidene) cyclopropanecarbaldehyde 7 in moderate to good yields. Plausible mechanisms for all these transformations have been discussed on the basis of the obtained results and control experiments. Copyright
A synthetic protocol of trans-substituted cyclopentenes via the ring-opening rearrangement of MCP alkenyl derivatives
Tang, Xiang-Ying,Shi, Min
supporting information; experimental part, p. 902 - 905 (2010/05/18)
(Chemical Equation Presented) A efficient method to stereospecifically synthesize trans-substituted cyclopentene derivatives via the ring-opening rearrangement of readily available MCP alkenyl derivatives in moderate to good yields has been described. The control experiment based on the deuterium labeling experiment and the addition of TEMPO revealed that this transformation might proceed through a fast concerted pericyclic process rather than a simple radical pathway or an ionic pathway.
