6‐Endo‐dig versus 5‐exo‐dig: Exploring Radical Cyclization Preference with First‐, Second‐, and Third‐row Linkers using High‐level Quantum Chemical Methods
Abstract:As an expansion upon Baldwin rules, the cyclization reactions of hex‐5‐yn‐1‐yl radical systems with different first‐, second‐, and third‐row linkers are explored at the CCSD(T) level via means of the SMD(benzene)‐G4(MP2) thermochemical protocol. Unlike C, O, and N linkers, systems with B, Si, P, S, Ge, As, and Se linkers are shown to favor 6‐endo‐dig cyclization. This offers fundamental insights into the rational synthetic design of cyclic compounds. A thorough analysis of stereoelectronic effects, cyclization… Show more
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