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Formation of complex cyclic compounds via a dehydrogenative Diels-Alder reaction
Zhongwei Xu1, Yu Lei1, Meng Chang1
1Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecular-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. yiminhu@ahnu.edu.cn.
None:
Reported herein is an unprecedented annulation strategy for macrocyclic compounds. This reaction facilitates the generation of α,3-dehydrotoluene (DHT) intermediates through a pentadehydro-Diels-Alder process, wherein subsequent DHT variants react with 1,6-diphenylhexa-1,3,5-triene to afford macrocyclic compounds with a broad substrate scope. Density functional theory computations support a zwitterionic intermediate process. Another product with a different skeleton is obtained by changing the reaction conditions.
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