1620005-31-3Relevant academic research and scientific papers
An unexpected double diels-alder reaction of (E)-2-bromo-4-aryl-1,3-pentadiene involving [1,5]-hydrogen migration and HBr elimination: Synthesis of bicyclo[2.2.2]octene derivatives
Huang, Pingping,Liu, Lingyan,Chang, Weixing,Li, Jing
supporting information, p. 548 - 552 (2015/09/16)
An unexpected double Diels-Alder (DDA) reaction of (E)-2-bromo-4-aryl-1,3-pentadiene was developed and resulted in a series of "butterfly-like" bicyclo [2.2.2]octene derivatives in moderate to good yields without the need for a metal catalyst. The proposed mechanism involves a [1,5]-sigmatropic hydrogen migration and HBr elimination. Through this decisive [1,5]-hydrogen shift step, the electronic properties and steric hindrance of the conjugated diene substrate are completely altered and the DDA reaction of this potential diene synthon is successfully achieved.
The metal tin promoted cascade reaction of ketones in aqueous media for the construction of 2-bromo-4-aryl-1,3-pentadiene
Liu, Lingyan,Zhang, Yan,Zhang, Hua,Huang, Kaimeng,Gao, Bo-Xin,Zou, Min,Zhou, Xin,Wang, Hongkai,Li, Jing
, p. 5393 - 5399 (2014/07/21)
A novel type of transformation was discovered serendipitously during the Barbier-type allenylation reaction of aromatic ketones promoted by the metal, tin, in aqueous media. Additionally, a series of new, highly functionalized 2-bromo-4-aryl-1,3-pentadienes could be obtained with good yields in this reaction. This cascade reaction shows the unique properties of the metal, tin. Furthermore, it is actually a cascade reaction which involves two steps: one is the Barbier-type allenylation of the carbonyl compound, and the other is an SN2′ type addition-elimination reaction. Notably, this reaction has the advantages of simple, mild conditions and is easy to operate. Furthermore, the corresponding product could be applied to various coupling reactions or other diversified transformations. This journal is the Partner Organisations 2014.
