136540-24-4Relevant academic research and scientific papers
The thermal conversions of 6,6-difluorobicyclo[3.1.0]hex-2-enes to fluorobenzenes. An interesting dichotomy of mechanisms
Dolbier Jr.,Keaffaber,Burkholder,Koroniak,Pradhan
, p. 9649 - 9660 (2007/10/02)
A kinetic study of the thermal, dehydrofluorinative aromatization reactions of two ostensibly-similar 6,6-difluorobicyclo[3.1.0]hex-2-ene systems led to the conclusion that drastically different mechanisms operate for the two reactions. Activation parameters, solvent effects, kinetic isotope effects, isotope labelling experiments and observation of reactive intermediates all contributed to the conclusion that the reaction of 6,6-difluorobicyclo[3.1.0]hex-2-ene, 1, proceeds via a homolytic hydrogen-shift rearrangement, while the reaction of 2,3-benzo-6,6-difluorobicyclo[3.1.0]hex-2-ene, 6, proceeds via a solvolytic mechanism involving rate-determining carbocation formation.
The thermal conversion of 6,6-difluorobicyclo[3.1.0]hex-2-ene to fluorobenzene. A novel mechanism
Dolbier Jr.,Keaffaber,Burkholder,Sellers,Koroniak,Pradhan
, p. 3933 - 3936 (2007/10/02)
The dehydrofluorinative aromatization reaction of 6,6-difluorobicyclo[3.1.0]hex-2-ene (1) has been found to proceed via a two-step mechanism, the first being a novel, rate-determining homolytic H-shift process.
