Bimolecular Formation of Radicals by H‐Transfer, 6. Uncatalyzed Transfer Hydrogenation of a Benzhydryl Fluoride by 9,10‐Dihydroanthracene

Abstract 1‐Adamantylfluorodiphenylmethane ( 2 ) was reduced to 1‐adamantyldiphenylmethane ( 3 ) when heated with 9,10‐dihydroanthracene to 330°C. From the second‐order kinetics, the activation parameters (Δ H ‡ = 37.2 ± 0.5 kcal mol −1 , Δ S ‡ = −18.8 ± 0.8 cal mol −1 K −1 ), the kinetic isotope effect k H / k D = 2.4 (373°C) [17] , and the observation of intermediate radical species by ESR it was concluded that the reaction is a new example of a molecule‐induced radical formation (MIRF) process. This is supported by thermochemical data.