35295-64-8Relevant academic research and scientific papers
SINGLE-PARAMETER VERSUS DUAL-PARAMETER CORRELATION FOR RADICAL REACTIONS. ADDITION OF BROMINE ATOMS TO α-METHYLSTYRENES
Jiang, Xi-Kui,Liu, Wayne Wei-Zhong,Wu, Shi-Hui
, p. 96 - 104 (2007/10/02)
A rigorous procedure was developed for measuring the relative rates of addition of bromine atoms to eleven substituted α-methylstyrenes (1-Y, with Y = CF3, NO2, F, CN, Cl, Br, CO2Me, Me, COMe, OMe and SMe).The reaction was run in tetrahydrofuran in the presence of HBr, O2 and dibutyl peroxyoxalate at 30 deg C.All products were derived from the YC6H4CMeCH2Br adduct radicals, which were immediately intercepted by O2.Correlation analysis of all the data confirmed the proposition that in the absence of measurable steric effects, the relative rates for radical additions can be correlated only by a dual-parameter equation and not by a single parameter equation.Among various combiations of ?* and ξx, the (?JJ* + ?mb) combination yields the best correlation.
Novel Transformations of 1,2-Dioxetanes: β-Hydroxy Ethers by Addition of Alkyllithium Reagents
Adam, Waldemar,Heil, Markus
, p. 235 - 241 (2007/10/02)
The reaction of 1,2-dioxetanes with alkyllithium reagents was investigated.The 3,3-disubstituted dioxetanes 2a,d and their halogen-substituted analogues 2b,c, which were used as probes to differentiate between the mechanistic alternatives (SN2 reactivity vs. single-electron transfer), reacted with n-BuLi to afford the β-hydroxy ethers 3a-d.Additionally, the epoxide 4 was obtained from dioxetanes 2b,c.The epoxide 5 and a small amount of acetophenone were found in the reaction of dioxetane 2c with triphenylmethyllithium, but only the minor part of the dioxetane-derived products could be identified.The observation of the epoxides 4 and 5 led to the mechanistic conclusion that nucleophilic attack (SN2 reactivity) is the most prominent process in this reaction.Key Words: Dioxetanes / Single electron transfer vs. nucleophilic attack / Ethers, β-hydroxy / Alkyllithium reagents
