Adamek Jakub, Mazurkiewicz Roman, Węgrzyk-Schlieter Anna
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Bolesława Krzywoustego 4, 44-100 Gliwice, Poland.
Biotechnology Center, Silesian University of Technology, Bolesława Krzywoustego 8, 44-100 Gliwice, Poland.
ACS Omega. 2022 Aug 15;7(34):30486-30494. doi: 10.1021/acsomega.2c03930. eCollection 2022 Aug 30.
Herein, we discuss the formation and reactivity of 1-imidocarbenium cations in Friedel-Crafts-type reaction between 1-imidoalkylphosphonium salts and arenes. The observed weakening of C-P bond is described qualitatively and quantitatively. The determination of rate constants and activation energies of C-P bond cleavage enabled systematic reactivity investigations of a series of phosphonium salts with different structures. Finally, the application scope for the imidoalkylation of aromatic hydrocarbons was explored. The results confirm that the generated 1-imidocarbenium cations are reactive enough to alkylate strongly activated, less-activated, or even inactivated aromatic compounds.
在此，我们讨论了1-亚氨基烷基鏻盐与芳烃之间的傅克型反应中1-亚氨基碳正离子的形成及其反应活性。对观察到的C-P键弱化进行了定性和定量描述。C-P键断裂速率常数和活化能的测定使得能够对一系列具有不同结构的鏻盐进行系统的反应活性研究。最后，探索了芳烃亚氨基烷基化的应用范围。结果证实，生成的1-亚氨基碳正离子具有足够的反应活性，能够使强活化、弱活化甚至未活化的芳香族化合物发生烷基化反应。
