Spectroscopic and computational evidence for the concerted mechanism of the Wagner‐Jauregg reaction

• DOI: 10.1002/poc.4140
• Publication Date: 2020-09-22T09:36:58Z
• Authors: Samuel S. Tartakoff; Abigail A. Enders; Wenyao Zhang; Adam D. Hill
• Keywords: Concerted reaction

Abstract The Wagner‐Jauregg reaction, despite its potential utility, has remained largely unexplored since discovery in 1930. Utilizing density functional theory (DFT) calculations and experimental 1 H nuclear magnetic resonance (NMR) kinetics data to generate a Hammett plot, the reaction is shown proceed via highly asynchronous, concerted mechanism, analogous Diels–Alder reaction. Our development of milder, more reliable conditions for will facilitate synthesis novel, structurally complex, polycyclic molecules.