40463-03-4Relevant academic research and scientific papers
Arylcyclopropane Photochemistry. Substituent Effects on the Photochemical 1,3-Hydrogen Migration of 1,1-Dimethyl-2-phenylcyclopropane
Hixson, Stephen S.,Gallucci, Charles R.
, p. 2711 - 2713 (2007/10/02)
Irradiation of 1,1-dimethyl-2-arylcyclopropanes 1a-g (Ar = p-CF3C6H4 (1a), m-CF3C6H4 (1b), p-CH3C6H4 (1c), m-CH3C6H4 (1d), C6H5 (1e), m-OCH3C6H4 (1f), p-OCH3C6H4 (1g) gave in every case a 2-methyl-4-aryl-1-butene (2a-g) via a 1,3-hydrogen migration, accompanied by lesser amounts of a 3-methyl-1-aryl-2-butene (3a-g).Rearrangement is a singlet-state process.Rate constants for rearrangement were determined from reactant fluorescence lifetimes and product quantum yields.The rates for rearrangament of 1 to 2 were as follows:1a, 25*106s-1; 1b,15*106s-1; 1c, 7.9*106s-1; 1d, 6.1*106s-1; 1e, 2.3*106s-1; 1f, 1.9*106s-1; 1g, 0.87*106s-1.It isconcluded that the energetics of cyclopropane ring opening are important in the rate-determining step of the reaction.
Reactivity of Aryl Vinyl Di-?-methane Systems. Mechanistic and Exploratory Organic Photochemistry
Zimmerman, Howard E.,Swafford, Richard L.
, p. 3069 - 3083 (2007/10/02)
The di-?-methane rearrangement of a series of meta and para substituted arylvinylmethane reactants was investigated with the aim of determiningthe patterns of reactivity in systems in which initial excitation is localized in the aryl moiety.Thus the photo
