1617526-39-2Relevant academic research and scientific papers
Lewis Acid Assisted Diels-Alder Reaction with Regio- and Stereoselectivity: Anti-1,4-Adducts with Rigid Scaffolds and Their Application in Explosives Sensing
Chen, Qi,Chen, Hao,Meng, Xiao,Ma, Yuguo
, p. 5016 - 5019 (2015)
Unusual anti-1,4-adducts of anthracene derivatives and anti-adducts of inert arenes with rigid scaffolds have been obtained via AlCl3-assisted Diels-Alder reaction in good to excellent yields under mild conditions. Further derivation of 1,4-adducts gave π-conjugated polymers which could act as sensors of explosive species. This highly efficient synthesis method provides versatile approaches to solid-state emissive π-conjugated polymers.
Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives
Chen, Hao,Yao, Erdong,Xu, Chi,Meng, Xiao,Ma, Yuguo
, p. 5102 - 5107 (2014/07/08)
Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.
