BIMOLECULAR FORMATION OF RADICALS BY H-TRANSFER .6. UNCATALYZED TRANSFER HYDROGENATION OF A BENZHYDRYL FLUORIDE BY 9,10-DIHYDROANTHRACENE

1-Adamantylfluorodiphenylmethane (2) was reduced to 1-adamantyldipheny lmethane (3) when heated with 9,10-dihydroanthracene to 330 degrees C. From the second-order kinetics, the activation parameters (Delta H-do uble dagger = 37.2 +/- 0.5 kcal mol(-1), Delta S-double dagger = -18.8 +/- 0.8 cal mol(-1) K-1), the kinetics isotope effect k(H)/k(D) = 2.4 (373 degrees C)([17]), and the observation of intermediate radical sp ecies by ESR it was concluded that the reaction is a new example of a molecule-induced radical formation (MIRF) process. This is supported b y thermochemical data.